Pub Date : 2019-01-01DOI: 10.14233/ajomc.2019.ajomc-p215
H. M. N. Kumari, Manjunath Harihara Mathada, Mahesh Kumar, K. Suda, K. Basavaraja
Present work reports the biologically important benzofuran aryl ureas and carbamates. The benzofuran ring was formed by reacting bromo salicylaldehyde with diethyl bromomalonate in presence of dry acetone and anhydrous potassium carbonate to obtain 5-bromo-2-ethyl carboxylate (1). The obtained ester (1) was converted into corresponding hydrazide (2) by treating with hydrazine hydrate in ethanol. Compound 2 was then converted into 5-bromobenzofuran-2-carbonyl azide (3) by treating it with sodium nitrite in dioxane and acetic acid. The compound 3 is converted into 5-bromobenzofuranyl aryl ureas (4a-e) after treating primary amines and anhydrous toluene. 5-Bromobenzofuranyl aryl carbamate (5) and ethyl carbamate (6) were also synthesized by treating compound 3 with substituted phenol in toluene and ethanol respectively. All the compounds were characterized by NMR, IR and screened for antimicrobial activities.
{"title":"Synthesis, Characterization, Antimicrobial Screening of 5-Bromobenzofuranyl Aryl Ureas and Carbamates","authors":"H. M. N. Kumari, Manjunath Harihara Mathada, Mahesh Kumar, K. Suda, K. Basavaraja","doi":"10.14233/ajomc.2019.ajomc-p215","DOIUrl":"https://doi.org/10.14233/ajomc.2019.ajomc-p215","url":null,"abstract":"Present work reports the biologically important benzofuran aryl ureas and carbamates. The benzofuran ring was formed by reacting bromo salicylaldehyde with diethyl bromomalonate in presence of dry acetone and anhydrous potassium carbonate to obtain 5-bromo-2-ethyl carboxylate (1). The obtained ester (1) was converted into corresponding hydrazide (2) by treating with hydrazine hydrate in ethanol. Compound 2 was then converted into 5-bromobenzofuran-2-carbonyl azide (3) by treating it with sodium nitrite in dioxane and acetic acid. The compound 3 is converted into 5-bromobenzofuranyl aryl ureas (4a-e) after treating primary amines and anhydrous toluene. 5-Bromobenzofuranyl aryl carbamate (5) and ethyl carbamate (6) were also synthesized by treating compound 3 with substituted phenol in toluene and ethanol respectively. All the compounds were characterized by NMR, IR and screened for antimicrobial activities.","PeriodicalId":8846,"journal":{"name":"Asian Journal of Organic & Medicinal Chemistry","volume":"18 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79420454","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-01-01DOI: 10.14233/AJOMC.2019.AJOMC-P209
Satyanarayan Sahoo, C. B. Rao
Formulation of poorly water-soluble drugs for oral drug delivery has always been a difficult task for formulation scientists. Lurasidone hydrochloride is one such agent which is used to control bipolar depre-ssion. The objective of this study was to formulate and optimize lurasi-done nanosuspension, further formulating optimized nanosuspensions as fast disintegrating tablets for improved patient compliance. In the present study, lurasidone nanosuspension was prepared by nanomilling technique. Optimized nanosuspension has mean particle diameter of 248.9 nm, polydispersity index of 0.127 and zeta potential of 18.1 mV. The lyophilized optimized nanocrystals, optimize nanosuspension as granulating fluid and as top spraying dispersion for granulation in fluid bed granulator being used to formulate fast disintegrating tablets with suitable super disintegrant. Croscarmellose sodium was found to be best superdisintegrant compared to sodium starch glycolate and crospovidone, as its acts by both mechanism swelling and wicking. Its swells 4-8 folds in less than 10 s. Many folds increase in the rate of drug release observed compare to micronized lurasidone and marketed product. There was no change in crystalline nature after nanomilling as characterized by XRD and FTIR, and it was found to be chemically stable with high drug content. The developed fast disintegrating tablets would be an alternative better formulation than its conventional formulation to address its bioavailability issue and for improved patient compliance. However, this should be further confirmed by appropriate in vivo studies.
{"title":"Design, Optimization and Evaluation of Lurasidone Hydrochloride Nanocrystals as Fast Disintegrating Tablets","authors":"Satyanarayan Sahoo, C. B. Rao","doi":"10.14233/AJOMC.2019.AJOMC-P209","DOIUrl":"https://doi.org/10.14233/AJOMC.2019.AJOMC-P209","url":null,"abstract":"Formulation of poorly water-soluble drugs for oral drug delivery has always been a difficult task for formulation scientists. Lurasidone hydrochloride is one such agent which is used to control bipolar depre-ssion. The objective of this study was to formulate and optimize lurasi-done nanosuspension, further formulating optimized nanosuspensions as fast disintegrating tablets for improved patient compliance. In the present study, lurasidone nanosuspension was prepared by nanomilling technique. Optimized nanosuspension has mean particle diameter of 248.9 nm, polydispersity index of 0.127 and zeta potential of 18.1 mV. The lyophilized optimized nanocrystals, optimize nanosuspension as granulating fluid and as top spraying dispersion for granulation in fluid bed granulator being used to formulate fast disintegrating tablets with suitable super disintegrant. Croscarmellose sodium was found to be best superdisintegrant compared to sodium starch glycolate and crospovidone, as its acts by both mechanism swelling and wicking. Its swells 4-8 folds in less than 10 s. Many folds increase in the rate of drug release observed compare to micronized lurasidone and marketed product. There was no change in crystalline nature after nanomilling as characterized by XRD and FTIR, and it was found to be chemically stable with high drug content. The developed fast disintegrating tablets would be an alternative better formulation than its conventional formulation to address its bioavailability issue and for improved patient compliance. However, this should be further confirmed by appropriate in vivo studies.","PeriodicalId":8846,"journal":{"name":"Asian Journal of Organic & Medicinal Chemistry","volume":"36 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85052746","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-01-01DOI: 10.14233/ajomc.2019.ajomc-p235
N. Mohan, V. Meera, J. Soja, M. Latha
Nipah virus is a highly pathogenic paramyxovirus belonging to the genus Henipavirus, classified as Biosafety Level 4 (BSL4) agents. The virus causes severe illness characterized by encephalitis or respiratory disease in human. The case-lethality rate of Nipah was reported to be 70 % in India, since year 2001. Despite the high pathogenicity of virus, no therapeutics are currently approved for use in human. But, ribavirin, favipiravir and human mono clonal antibody was found to reduce the intensity in early stage. Medicinal plants serve as a rich source of therapeutically active compounds. Nyctanthus arbortristis Linn or pavizhamalli (Harsinger) is traditionally known to have activity against Nipha virus. In this study, therapeutic activity of phytochemicals arbortristoside A and arbortristoside C present in pavizhamalli plant against Nipha virus target was investigated by computational docking simulation. Computational docking analysis was performed using Schrodinger Suite. The phytochemicals arbortristoside A and arbortristoside C show promising binding affinity with the target Nipah virus than the reference drugs. Results of the study could be advantageous to develop a new lead molecule against Nipah virus infection.
{"title":"in silico Docking Analysis of Small Molecule Inhibitors from\u0000Nyctanthes arbor-tristis against Nipah Virus Infection","authors":"N. Mohan, V. Meera, J. Soja, M. Latha","doi":"10.14233/ajomc.2019.ajomc-p235","DOIUrl":"https://doi.org/10.14233/ajomc.2019.ajomc-p235","url":null,"abstract":"Nipah virus is a highly pathogenic paramyxovirus belonging to the genus Henipavirus, classified as Biosafety Level 4 (BSL4) agents. The virus causes severe illness characterized by encephalitis or respiratory disease in human. The case-lethality rate of Nipah was reported to be 70 % in India, since year 2001. Despite the high pathogenicity of virus, no therapeutics are currently approved for use in human. But, ribavirin, favipiravir and human mono clonal antibody was found to reduce the intensity in early stage. Medicinal plants serve as a rich source of therapeutically active compounds. Nyctanthus arbortristis Linn or pavizhamalli (Harsinger) is traditionally known to have activity against Nipha virus. In this study, therapeutic activity of phytochemicals arbortristoside A and arbortristoside C present in pavizhamalli plant against Nipha virus target was investigated by computational docking simulation. Computational docking analysis was performed using Schrodinger Suite. The phytochemicals arbortristoside A and arbortristoside C show promising binding affinity with the target Nipah virus than the reference drugs. Results of the study could be advantageous to develop a new lead molecule against Nipah virus infection.","PeriodicalId":8846,"journal":{"name":"Asian Journal of Organic & Medicinal Chemistry","volume":"80 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82363466","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-01-01DOI: 10.14233/AJOMC.2019.AJOMC-P179
V. Tripathi, N. Saxena
A library of new dihydropyrazole derivatives have been synthesized from well designed curcumin analogues by reaction of chalcone derivatives with phenylhydrazine. All the synthesized compounds were characterized by spectroscopic (1H and 13C NMR, IR spectra), spectrometric (Mass spectra) data and elemental analysis. Dihydro-pyrazoles exhibited characteristic dd (double doublet) due to presence of optically active carbon of pyrazole ring. All the synthesized compounds were also evaluated for their antifungal potential against six different fungal starins. Evaluated heterocyles showed potent inhibitory property against tested fungal strains with minimum inhibitory concentration (MIC) values upto 3.12 μg/mL. Heterocyles with nitro and methoxy substitutions were showing best antifungal activities. Among 20 different derivatives tested for biological activity SAR has been developed between the various substitutions at phenyl ring of synthesized heterocycles.
{"title":"Synthesis and Antifungal Activity of New Dihydropyrazoles of Designed Curcumin Analogues","authors":"V. Tripathi, N. Saxena","doi":"10.14233/AJOMC.2019.AJOMC-P179","DOIUrl":"https://doi.org/10.14233/AJOMC.2019.AJOMC-P179","url":null,"abstract":"A library of new dihydropyrazole derivatives have been synthesized from well designed curcumin analogues by reaction of chalcone derivatives with phenylhydrazine. All the synthesized compounds were characterized by spectroscopic (1H and 13C NMR, IR spectra), spectrometric (Mass spectra) data and elemental analysis. Dihydro-pyrazoles exhibited characteristic dd (double doublet) due to presence of optically active carbon of pyrazole ring. All the synthesized compounds were also evaluated for their antifungal potential against six different fungal starins. Evaluated heterocyles showed potent inhibitory property against tested fungal strains with minimum inhibitory concentration (MIC) values upto 3.12 μg/mL. Heterocyles with nitro and methoxy substitutions were showing best antifungal activities. Among 20 different derivatives tested for biological activity SAR has been developed between the various substitutions at phenyl ring of synthesized heterocycles.","PeriodicalId":8846,"journal":{"name":"Asian Journal of Organic & Medicinal Chemistry","volume":"27 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89490573","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-01-01DOI: 10.14233/AJOMC.2019.AJOMC-P159
Sandhya Chhakra, A. Mukherjee, Harlal Singh, S. Chauhan
An efficient synthesis of novel 2,3,4-trisubstituted 1,5-benzothiazepines (4a-e) incorporating the sulfonyl group is described. Compound (4a-e) was synthesized by the reaction of 3-(1,4-dioxane-6-sulfonyl)-2,4-dimethyl/4-methyl-2-phenyl/2,4-diphenyl/2-ethoxy-4-methyl/2,4-diethoxy propane-1,3-dione (3ae) with 2-aminobenzenethiol with ZnOnanoparticles/pyridine. Formation of compound (3a-e) was achieved by the reaction of 1,4-dioxane-6-sulfonyl chloride (1) with 2,4-dimethyl/4-methyl-2-phenyl/2,4-diphenyl/2-ethoxy-4-methyl/2,4-diethoxy propane-1,3-dione (2a-e). The benzothiazepines (4a-e) obtained were purified by column chromatography (benzene: CHCl3, 40:60, 30:70, 20:80, 10:90) and crystallized from methanol. The purity of the compounds was checked by TLC using (CHCl3: CH3OH, 9:1) as the mobile phase. The structure of the compounds has been established by elemental, IR, 1H NMR, 13C NMR and Mass spectral analyses. Frontier molecular orbitals of the title compounds have been studied in the ground state speculatively. The reactivity of a molecule using diverse descriptors such as softness, electrophilicity, electronegativity, HOMO-LUMO energy gap is calculated additionally discussed.
{"title":"Synthesis of Novel Substituted 1,5-Benzothiazepines Containing 1,4-Benzodioxane Sulfonyl Moiety","authors":"Sandhya Chhakra, A. Mukherjee, Harlal Singh, S. Chauhan","doi":"10.14233/AJOMC.2019.AJOMC-P159","DOIUrl":"https://doi.org/10.14233/AJOMC.2019.AJOMC-P159","url":null,"abstract":"An efficient synthesis of novel 2,3,4-trisubstituted 1,5-benzothiazepines (4a-e) incorporating the sulfonyl group is described. Compound (4a-e) was synthesized by the reaction of 3-(1,4-dioxane-6-sulfonyl)-2,4-dimethyl/4-methyl-2-phenyl/2,4-diphenyl/2-ethoxy-4-methyl/2,4-diethoxy propane-1,3-dione (3ae) with 2-aminobenzenethiol with ZnOnanoparticles/pyridine. Formation of compound (3a-e) was achieved by the reaction of 1,4-dioxane-6-sulfonyl chloride (1) with 2,4-dimethyl/4-methyl-2-phenyl/2,4-diphenyl/2-ethoxy-4-methyl/2,4-diethoxy propane-1,3-dione (2a-e). The benzothiazepines (4a-e) obtained were purified by column chromatography (benzene: CHCl3, 40:60, 30:70, 20:80, 10:90) and crystallized from methanol. The purity of the compounds was checked by TLC using (CHCl3: CH3OH, 9:1) as the mobile phase. The structure of the compounds has been established by elemental, IR, 1H NMR, 13C NMR and Mass spectral analyses. Frontier molecular orbitals of the title compounds have been studied in the ground state speculatively. The reactivity of a molecule using diverse descriptors such as softness, electrophilicity, electronegativity, HOMO-LUMO energy gap is calculated additionally discussed.","PeriodicalId":8846,"journal":{"name":"Asian Journal of Organic & Medicinal Chemistry","volume":"33 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87948380","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-01-01DOI: 10.14233/ajomc.2019.ajomc-p177
A. Nagaraj, S. Srinivas, P. R. Naik, R. Neelofer
A series of new 6-(2-oxo-3-[(4-arylpiperazino)carbonyl]-2H-6-chromenyl-methyl)-3-[(4- arylpiperazino)carbonyl]-2H-2-chromenone 9(a-j) have been synthesized and tested for their antibacterial activity against human pathogenic strains. The antibacterial evaluation data revealed that the compounds containing 4-methoxyphenyl, 4-fluorophenyl, 4-nitrophenyl and 4-hydroxyphenyl moieties at 4-position of the piperazine ring exhibited potent inhibitory activity towards all the tested bacterial strains. Further, the compounds containing phenyl and 4-methylphenyl moieties showed good activity towards P. aeruginosa and C. violaceum. The 4-nitrophenyl moiety also showed potent activity towards B. subtilis and B. sphaericus.
{"title":"Synthesis and Antibacterial Study of Novel Piperazine Linked Methylene-bis-Coumarins","authors":"A. Nagaraj, S. Srinivas, P. R. Naik, R. Neelofer","doi":"10.14233/ajomc.2019.ajomc-p177","DOIUrl":"https://doi.org/10.14233/ajomc.2019.ajomc-p177","url":null,"abstract":"A series of new 6-(2-oxo-3-[(4-arylpiperazino)carbonyl]-2H-6-chromenyl-methyl)-3-[(4- arylpiperazino)carbonyl]-2H-2-chromenone 9(a-j) have been synthesized and tested for their antibacterial activity against human pathogenic strains. The antibacterial evaluation data revealed that the compounds containing 4-methoxyphenyl, 4-fluorophenyl, 4-nitrophenyl and 4-hydroxyphenyl moieties at 4-position of the piperazine ring exhibited potent inhibitory activity towards all the tested bacterial strains. Further, the compounds containing phenyl and 4-methylphenyl moieties showed good activity towards P. aeruginosa and C. violaceum. The 4-nitrophenyl moiety also showed potent activity towards B. subtilis and B. sphaericus.","PeriodicalId":8846,"journal":{"name":"Asian Journal of Organic & Medicinal Chemistry","volume":"7 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78858919","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-01-01DOI: 10.14233/AJOMC.2019.AJOMC-P173
Monika Kakadiya, S. Ramiya, M. Noolvi, T. Pasha
Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis, with high level of mortality worldwide, currently with approximately 10 million cases of tuberculosis. These rate of incidence are due to several factors such as bacterial resistance, AIDS, latent tuberculosis that reoccur in patient. Deazaflavin dependent nitroreductase (Ddn) is an emerging target in the field of antitubercular agent. Ddn catalyses the reduction of nitroimidazoles resulting in intra-cellular release of lethal reactive nitrogen species. Nitroimidazole class drug- delamanid and pretonamid are used in the treatment of MDR-TB. In this present study, 26 new nitroimidazole derivatives were designed and docked into Ddn enzyme. In docking study, compounds 3, 5, 15, 16, 17, 18 and 21 showed similar interaction with amino acid residues such as Tyr 65, Ser 78, Tyr 136 as pretonamid reference drug and highest docking score and better ADMET compatibility. The ADMET prediction docking study of new designed compound revealed that the compounds 3, 16, 17 and 21 showed good binding with Ddn. In future it may be good and effective lead for development of antitubercular agent.
{"title":"Designing of Nitroimidazole Derivatives as a Promising Target for Treatment of Tuberculosis","authors":"Monika Kakadiya, S. Ramiya, M. Noolvi, T. Pasha","doi":"10.14233/AJOMC.2019.AJOMC-P173","DOIUrl":"https://doi.org/10.14233/AJOMC.2019.AJOMC-P173","url":null,"abstract":"Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis, with high level of mortality worldwide, currently with approximately 10 million cases of tuberculosis. These rate of incidence are due to several factors such as bacterial resistance, AIDS, latent tuberculosis that reoccur in patient. Deazaflavin dependent nitroreductase (Ddn) is an emerging target in the field of antitubercular agent. Ddn catalyses the reduction of nitroimidazoles resulting in intra-cellular release of lethal reactive nitrogen species. Nitroimidazole class drug- delamanid and pretonamid are used in the treatment of MDR-TB. In this present study, 26 new nitroimidazole derivatives were designed and docked into Ddn enzyme. In docking study, compounds 3, 5, 15, 16, 17, 18 and 21 showed similar interaction with amino acid residues such as Tyr 65, Ser 78, Tyr 136 as pretonamid reference drug and highest docking score and better ADMET compatibility. The ADMET prediction docking study of new designed compound revealed that the compounds 3, 16, 17 and 21 showed good binding with Ddn. In future it may be good and effective lead for development of antitubercular agent.","PeriodicalId":8846,"journal":{"name":"Asian Journal of Organic & Medicinal Chemistry","volume":"1 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89510860","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-01-01DOI: 10.14233/AJOMC.2019.AJOMC-P144
Mamta Sharma, S. Tomar
In this paper, we report the synthesis of a highly photocatalytic titanium dioxide nanoparticles bondedwith azobenzene and cotton by simple sol-gel method. The synthesized azobenzene based titania nanoparticles coated cotton fibers were characterized using UV-visible and SEM and reported their antimicrobial activity. It was observed that the presence of titanium dioxide bonded with azobenzene effectively prevents both the cotton fibers from getting contaminated.
{"title":"Synthesis and Antimicrobial Activity of Azobenzene Based Titania Nanoparticles Coated Cotton Fibers","authors":"Mamta Sharma, S. Tomar","doi":"10.14233/AJOMC.2019.AJOMC-P144","DOIUrl":"https://doi.org/10.14233/AJOMC.2019.AJOMC-P144","url":null,"abstract":"In this paper, we report the synthesis of a highly photocatalytic titanium dioxide nanoparticles bondedwith azobenzene and cotton by simple sol-gel method. The synthesized azobenzene based titania nanoparticles coated cotton fibers were characterized using UV-visible and SEM and reported their antimicrobial activity. It was observed that the presence of titanium dioxide bonded with azobenzene effectively prevents both the cotton fibers from getting contaminated.","PeriodicalId":8846,"journal":{"name":"Asian Journal of Organic & Medicinal Chemistry","volume":"45 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85967650","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-01-01DOI: 10.14233/AJOMC.2019.AJOMC-P161
R. Wanare
Reaction of 3-methyl-5-(3'-aryl prop-2'-enoyl)-1,2-benzisoxazole (1a-j) with thiourea and alcoholic solution of KOH afforded 3-methyl-5-(4'-aryl-2'-thiopyrimidin-6'-yl)-1,2-benzisoxazoles (2a-j). Oxidation of products 2a-j using alkaline KMnO4 solution produces 5-(4'-aryl-2'-thiopyrimidin-6'-yl)-1,2-benzisoxazole-3-carboxylic acids (3a-j). Condensation of products 3a-j with 2,3,4,6-tetra-Oacetyl-α-D-glucopyranosyl bromide (TAGBr), the glucosylating agent synthesized 3-(2,3,4,6-tetra-O-acetyl-3-acetyl-β-D-glucopyranosyl)-5-(4'-aryl-2'-thiopyrimidin-6'-yl)-1,2-benzisoxazoles (4a-j). Subsequent deacetylation of compounds 4a-j were carried out with CH3ONa furnishes β-Dglucopyranosyl-5-(4'-aryl-2'-thiopyrimidin-6'-yl)-1,2-benzisoxazole-3-carboxylates (5a-j). All the synthesized compounds were analyzed by elemental analysis (C, H and N), FT-IR, 1H NMR and mass spectral data. Most of the prepared compounds were analyzed their antibacterial and antifungal activities by cup-plate method. The present approach offers several advantages such as shorter reaction times, cleaner reactions, good yields, low-cost reagent and mild reaction conditions.
3-甲基-5-(3′-芳基-2′-烯基)-1,2-苯并恶唑(1a-j)与硫脲和KOH的酒精溶液反应得到3-甲基-5-(4′-芳基-2′-硫代嘧啶-6′-基)-1,2-苯并恶唑(2a-j)。用碱性KMnO4溶液氧化产物2a-j，得到5-(4′-芳基-2′-硫代嘧啶-6′-基)-1,2-苯并异恶唑-3-羧酸(3a-j)。产物3a-j与2,3,4,6-四乙酰基-α- d -葡萄糖吡喃基溴(TAGBr)缩合，糖基化剂合成3-(2,3,4,6-四- o -乙酰基-3-乙酰基-β- d -葡萄糖吡喃基)-5-(4'-芳基-2'-硫代嘧啶-6'-基)-1,2-苯并异恶唑(4a-j)。随后，化合物4a-j用CH3ONa进行去乙酰化，得到β-二葡萄糖吡喃基-5-(4'-芳基-2'-硫代嘧啶-6'-基)-1,2-苯并异恶唑-3-羧酸盐(5a-j)。通过元素分析(C、H、N)、红外光谱(FT-IR)、核磁共振氢谱(1H NMR)和质谱对合成的化合物进行了分析。用杯盘法分析了大部分化合物的抑菌和抗真菌活性。该方法具有反应时间短、反应干净、产率高、试剂成本低、反应条件温和等优点。
{"title":"A Novel and Facile Synthesis of Thiopyrimidines and O-Glucosides","authors":"R. Wanare","doi":"10.14233/AJOMC.2019.AJOMC-P161","DOIUrl":"https://doi.org/10.14233/AJOMC.2019.AJOMC-P161","url":null,"abstract":"Reaction of 3-methyl-5-(3'-aryl prop-2'-enoyl)-1,2-benzisoxazole (1a-j) with thiourea and alcoholic solution of KOH afforded 3-methyl-5-(4'-aryl-2'-thiopyrimidin-6'-yl)-1,2-benzisoxazoles (2a-j). Oxidation of products 2a-j using alkaline KMnO4 solution produces 5-(4'-aryl-2'-thiopyrimidin-6'-yl)-1,2-benzisoxazole-3-carboxylic acids (3a-j). Condensation of products 3a-j with 2,3,4,6-tetra-Oacetyl-α-D-glucopyranosyl bromide (TAGBr), the glucosylating agent synthesized 3-(2,3,4,6-tetra-O-acetyl-3-acetyl-β-D-glucopyranosyl)-5-(4'-aryl-2'-thiopyrimidin-6'-yl)-1,2-benzisoxazoles (4a-j). Subsequent deacetylation of compounds 4a-j were carried out with CH3ONa furnishes β-Dglucopyranosyl-5-(4'-aryl-2'-thiopyrimidin-6'-yl)-1,2-benzisoxazole-3-carboxylates (5a-j). All the synthesized compounds were analyzed by elemental analysis (C, H and N), FT-IR, 1H NMR and mass spectral data. Most of the prepared compounds were analyzed their antibacterial and antifungal activities by cup-plate method. The present approach offers several advantages such as shorter reaction times, cleaner reactions, good yields, low-cost reagent and mild reaction conditions.","PeriodicalId":8846,"journal":{"name":"Asian Journal of Organic & Medicinal Chemistry","volume":"14 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88582353","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-01-01DOI: 10.14233/ajomc.2019.ajomc-p189
R. Kamani, Rahul P. Thummar, Nirav H. Sapariya, Beena K. Vaghasiya, Jemin R. Avalani, Vishal B. Purohit, K. Patel, Dipak K. Raval
The synthesis of a novel tolylthiopyrazol bearing methyl group has been achieved by transition metal free N-chlorosuccinimide mediated direct sulfenylation of 1-aryl pyrazolones at room temperature. The product obtained was characterized by spectroscopic techniques and finally confirmed by X-ray diffraction studies. The compound 1-(2-chlorophenyl)-3-methyl-4-(p-tolylthio)-1H-pyrazol-5-ol (m.f. C17H15N2OSCl) crystallizes in monoclinic crystal class in space group P21/c with cell parameters a = 9.6479(5) Å, b = 15.1233(8) Å, c = 11.4852(6) Å, β = 108.374(2)°, V=1590.4(2) Å3 and Z = 4. The final residual factor R1 = 0.0499.
采用无过渡金属的n -氯丁二酰亚胺介导1-芳基吡唑酮在室温下直接磺化，合成了一种含甲基的新型甲基硫代吡唑。所得产物经光谱技术表征，最后经x射线衍射研究证实。化合物1-(2-氯苯基)-3-甲基-4-(p-甲基硫)- 1h -吡唑-5-醇(m.f. C17H15N2OSCl)在P21/c空间群中以单斜晶类结晶，晶型参数a =9.6479(5) Å， b = 15.1233(8) Å， c = 11.4852(6) Å， β = 108.374(2)°，V=1590.4(2) Å3, Z = 4。最终剩余因子R1 = 0.0499。
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