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Synthesis and Antiproliferative Activity of Some Quinoline and Oxadiazole Derivatives 一些喹啉和恶二唑衍生物的合成及其抗增殖活性
Pub Date : 2016-11-24 DOI: 10.1155/2016/9589517
M. Ahsan, S. Shastri, R. Yadav, M. Hassan, M. Bakht, S. S. Jadav, S. Yasmin
In continuance of our search for newer antiproliferative agents we report herein the synthesis and antiproliferative studies of two series (5a–j and 10a–c) of heterocyclic compounds. All the new compounds were characterized by IR, NMR, and mass spectral data. The antiproliferative activity of 10 compounds (5a–j) was carried out on HeLa (cervix cancer cell line) and MDA-MB-435 (melanoma) and LC50, TGI, and GI50 were calculated, while the antiproliferative activity of 3 compounds (10a–c) was carried out against nine different panels of nearly 60 cell lines (NCI-60) according to the National Cancer Institute (NCI US) Protocol at 10 μM. 1-(7-Hydroxy-4-methyl-2-oxoquinolin-1(2H)-yl)-3-(4-methoxylphenyl)urea (5j) was found to have antiproliferative activity with GI50 of 35.1 μM against HeLa (cervix cancer cell line) and 60.4 μM against MDA-MB-435 (melanoma), respectively. The compounds 10a, 10b, and 10c showed antiproliferative activity with comparatively higher selectivity towards HOP-92 (Non-Small Cell Lung Cancer) with percent growth inhibitions (GIs) of 34.14, 35.29, and 31.59, respectively.
为了继续寻找新的抗增殖药物,我们在此报告了两个系列(5a-j和10a-c)杂环化合物的合成和抗增殖研究。所有新化合物都通过IR、NMR和质谱数据进行了表征。10种化合物(5a-j)对HeLa(宫颈癌细胞系)和MDA-MB-435(黑色素瘤)的抗增殖活性进行了计算,并计算了LC50、TGI和GI50, 3种化合物(10a-c)对近60株NCI-60细胞系的9个不同组(10 μM)的抗增殖活性,根据美国国家癌症研究所(NCI US)的协议。1-(7-羟基-4-甲基-2-氧喹啉-1(2H)-yl)-3-(4-甲氧基苯基)尿素(5j)对HeLa(宫颈癌细胞株)和MDA-MB-435(黑色素瘤)的抗增殖活性分别为35.1 μM和60.4 μM。化合物10a、10b和10c对非小细胞肺癌(Non-Small Cell Lung Cancer, HOP-92)具有较高的选择性,其生长抑制率(gi)分别为34.14%、35.29%和31.59%。
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引用次数: 13
Synthesis of New Energetic Materials and Ionic Liquids Derived from Metronidazole 甲硝唑衍生新型含能材料及离子液体的合成
Pub Date : 2016-01-14 DOI: 10.1155/2016/4705809
M. A. Romero
Simple and efficient synthetic procedures were established for the preparation of new energetic covalent compounds, salts, and protonated ionic liquids based on the readily available antimicrobial agent metronidazole. Some of these materials exhibit the desirable properties of energetic materials and energetic ionic liquids, such as low vapor pressure, low melting point, good chemical and thermal stability, and high energetic content. For each of the relevant compounds prepared, thermal stability was determined by differential scanning calorimetry. Some of these compounds may be considered promising precursors of pharmaceuticals such as antimicrobial, antiparasitic, antifungal, antineoplastic agents, or enzyme inhibitors.
建立了以现有抗菌剂甲硝唑为基础,制备新型高能共价化合物、盐和质子化离子液体的简单高效的合成方法。其中一些材料表现出含能材料和含能离子液体的理想特性,如蒸气压低、熔点低、化学和热稳定性好、含能高。用差示扫描量热法测定了所制备化合物的热稳定性。其中一些化合物可能被认为是有前途的药物前体,如抗菌剂、抗寄生虫剂、抗真菌剂、抗肿瘤剂或酶抑制剂。
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引用次数: 6
Synthesis, Structural Elucidation, and Antibacterial Evaluation of Some New Molecules Derived from Coumarin, 1,3,4-Oxadiazole, and Acetamide 香豆素、1,3,4-恶二唑和乙酰胺新分子的合成、结构解析及抗菌性能评价
Pub Date : 2016-01-01 DOI: 10.1155/2016/8696817
S. Rasool, Aziz‐ur‐Rehman, M. Abbasi, S. Z. Siddiqui, S. A. Shah, S. Hassan, I. Ahmad
Because of the reported biological activities of coumarin, 1,3,4-oxadiazole, and acetamides, some new compounds incorporating these moieties were synthesized and evaluated for their biological potential against Gram-positive and Gram-negative bacteria. In the present work, 4-chlororesorcinol (1) and ethyl acetoacetate (2) were mixed in a strong acidic medium to synthesize 6-chloro-7-hydroxy-4-methyl-2-oxo-2H-chromene (3) which was subjected to the intermolecular cyclization after consecutive three steps to synthesize 5-(6-chloro-4-methyl-2-oxo-2H-chromen-7-yl)oxy]-1,3,4-oxadiazol-2-thiol (6). A series of acetamoyl electrophiles, 8a–o, were synthesized from aralkyl/alkyl/aryl amines, 7a–o, in an aqueous basic medium. The final compounds, 9a–o, were synthesized by the reaction of compounds 6 and 8a–o in DMF/NaH. The synthesized compounds were structurally elucidated by spectral data analysis of IR, 1H-NMR, and EIMS. The most of the synthesized compounds remained moderate to excellent antibacterial agents. The molecules, 9e, 9j, and 9k, were the most efficient ones against all the five bacterial strains taken into account.
由于香豆素、1,3,4-恶二唑和乙酰胺的生物活性已被报道,一些含有这些基团的新化合物被合成并评估了它们对革兰氏阳性和革兰氏阴性细菌的生物潜力。在目前的工作,4-chlororesorcinol(1)和乙酰乙酸乙酯(2)在强酸性介质混合合成6-chloro-7-hydroxy-4-methyl-2-oxo-2H-chromene(3)受到了分子间的环化后连续三个步骤合成5 - (6-chloro-4-methyl-2-oxo-2H-chromen-7-yl)氧]1,3,4-oxadiazol-2-thiol(6)。一系列acetamoyl亲电试剂,8光学,合成了芳烷基/烷基芳基胺,7光学,水基本的媒介。化合物6和8a-o在DMF/NaH中反应合成最终化合物9a-o。通过IR、1H-NMR和EIMS对合成的化合物进行了结构表征。大多数合成的化合物仍然是中等到优异的抗菌剂。9e、9j和9k分子对所有5种细菌菌株都是最有效的。
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引用次数: 1
Synthesis, Characterization, and Application of Poly(N,N′-dibromo-N-ethylnaphthyl-2,7-disulfonamide) as an Efficient Reagent for the Synthesis of 2-Arylbenzimidazole and 2-Aryl-1-arylmethyl-1H-1,3-benzimidazole Derivatives 聚(N,N′-二溴-N-乙基萘-2,7-二磺酰胺)作为合成2-芳基苯并咪唑和2-芳基-1-芳基甲基- 1h -1,3-苯并咪唑衍生物的高效试剂的合成、表征及应用
Pub Date : 2015-05-06 DOI: 10.1155/2015/635630
Vida Saleh, A. Khazaei, Hamid Abizadeh, Shahnaz Saednia
The condensation of O-phenylenediamine (OPD) with aryl aldehydes is carried out in acetonitrile using poly(N,N′-dibromo-N-ethylnaphthyl-2,7-disulfonamide) (PBNS) as a novel and heterogeneous catalyst. PBNS has some potential advantages which include ease of separation from the reaction mixture by simple filtration, easy preparation, recoverablility, convenience, and stability under normal condition and also is not dangerous as molecular bromine.
以聚(N,N ' -二溴-N-乙基萘-2,7-二磺酰胺)(PBNS)为新型多相催化剂,在乙腈中进行了邻苯二胺(OPD)与芳基醛的缩合反应。PBNS具有过滤简单、制备简单、可回收性好、使用方便、在正常条件下稳定等优点,而且不具有分子溴的危险性。
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引用次数: 1
Insight into the Willgerodt-Kindler Reaction of ω-Haloacetophenone Derivatives: Mechanistic Implication ω-卤代苯乙酮衍生物的wilgerodt - kindler反应:机理意义
Pub Date : 2014-12-10 DOI: 10.1155/2014/486540
Urbain C. Kasséhin, F. Gbaguidi, C. N. Kapanda, C. McCurdy, J. Poupaert
This paper reports efforts aimed at tuning up the synthesis of a compound library centered on the general template 2-amino-1-phenyl-2-thioxoethanone taking the condensation of ω-haloacetophenone, octasulfur, and morpholine as pilot reaction. Considerations about atomic economy were found extremely precious in selecting the best starting halo-reagent. A one-pot practical method based on use of 2-bromo-1-phenylethanone as substrate and N,N-dimethylformamide as solvent can be easily scaled up to gram amounts (72% yield). Based on this synthetic approach, some more specific examples are reported.
本文报道了以ω-卤代苯乙酮、八硫脲和啉的缩合反应为先导反应,以2-氨基-1-苯基-2-硫代硫代乙酮为中心合成化合物库的工作。在选择最佳的起始光晕试剂时,原子经济性是非常重要的。以2-溴-1-苯乙酮为底物,N,N-二甲基甲酰胺为溶剂的一锅实用方法可以很容易地扩大到克量(收率为72%)。在此综合方法的基础上,还报道了一些更具体的例子。
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引用次数: 2
Microwave-Assisted Synthesis of Some 1,3,4-Oxadiazole Derivatives and Evaluation of Their Antibacterial and Antifungal Activity 微波辅助合成1,3,4-恶二唑衍生物及其抑菌活性评价
Pub Date : 2014-12-03 DOI: 10.1155/2014/694060
Deepak Swarnkar, R. Ameta, Ritu Vyas
A series of substituted 1,3,4-oxadiazole derivatives (3a–f) and (6a–f) have been synthesized from diphenylacetic acid hydrazide under microwave irradiation in various reaction conditions. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, and 1H NMR. These targeted compounds have been tested for their antibacterial and antifungal activities compared to ampicillin and griseofulvin as standard drug. Compounds 3a, 3e, 3f, 6c, 6d, 6e, and 6d exhibited the maximum antibacterial activities while 3b, 3c, 3d, 3e, 6a, 6d, and 6e exhibited the maximum antifungal activities.
以二苯乙酸肼为原料,在微波照射下,在不同的反应条件下合成了一系列取代的1,3,4-恶二唑衍生物(3a-f)和(6a-f)。通过元素分析、红外光谱和核磁共振氢谱确定了合成化合物的结构。与氨苄西林和灰黄霉素作为标准药物相比,对这些靶向化合物的抗菌和抗真菌活性进行了测试。化合物3a、3e、3f、6c、6d、6e和6d抑菌活性最强,化合物3b、3c、3d、3e、6a、6d和6e抑菌活性最强。
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引用次数: 7
Synthesis, Characterization, and Evaluation for Antibacterial and Antifungal Activities of N-Heteroaryl Substituted Benzene Sulphonamides n -杂芳基取代苯磺酰胺的合成、表征及抑菌活性评价
Pub Date : 2014-11-27 DOI: 10.1155/2014/419518
Christiana Nonye Igwe, U. Okoro
The synthesis and biological activity of N-heteroaryl substituted benzene sulphonamides (3a–h) were successful. Simple condensation reaction of benzene sulphonyl chloride (1) with substituted heteroaromatic compounds (2a–h) under dry pyridine and acetone gave the target molecules (3a–h) in good to excellent yield. The compounds were characterized using FTIR, 1HNMR, and 13CNMR. The compounds were screened for antibacterial activity against E. coli, Salmonella typhi, P. aeruginosa, B. cereus, K. pneumonia, and Sarcina  lutea and antifungal activity against C. albicans and A. niger. The results of the antimicrobial activity showed improved biological activity against some tested organisms.
成功合成了n -杂芳基取代苯磺酰胺(3a-h),并对其生物活性进行了研究。苯磺酰氯(1)与取代的杂芳香化合物(2a-h)在干吡啶和丙酮的作用下进行简单缩合反应,得到了产率良好至优异的目标分子(3a-h)。用FTIR、1HNMR和13CNMR对化合物进行了表征。筛选化合物对大肠杆菌、伤寒沙门菌、铜绿假单胞菌、蜡样芽孢杆菌、肺炎克雷伯菌和黄斑病弧菌的抑菌活性以及对白色念珠菌和黑曲霉的抑菌活性。抑菌活性结果表明,对某些被试生物的抑菌活性有所提高。
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引用次数: 8
Proline Based Chiral Ionic Liquids for Enantioselective Michael Reaction 基于脯氨酸的手性离子液体用于对映选择性迈克尔反应
Pub Date : 2014-11-20 DOI: 10.1155/2014/836126
K. Nobuoka, S. Kitaoka, T. Kojima, Y. Kawano, Kazuya Hirano, M. Tange, S. Obata, Yuki Yamamoto, Thomas Harran, Y. Ishikawa
Chiral ionic liquids, starting from (S)-proline, have been prepared and evaluated the ability of a chiral catalyst. In Michael reaction of trans-β-nitrostyrene and cyclohexanone, all the reactions were carried out under homogeneous conditions without any solvent except for excess cyclohexanone. The chiral ionic liquid catalyst with the positive charge delocalized bulky pyrrolidinium cation shows excellent yields (up to 92%), diastereoselectivities (syn/anti = 96/4), and enantioselectivities (up to 95% ee) and could be reused at least three times without any loss of its catalytic activity. Such results demonstrated a promising new approach for green and economic chiral synthesis by using the chiral ionic liquids as a chiral catalyst and a chiral medium.
本文制备了以(S)-脯氨酸为起始原料的手性离子液体,并对其手性催化剂的性能进行了评价。反式β-硝基苯乙烯与环己酮的Michael反应除过量的环己酮外均在均相条件下进行。该手性离子液体催化剂具有良好的产率(高达92%)、非对映选择性(正/反= 96/4)和对映选择性(高达95% ee),并且可以重复使用至少三次而不损失其催化活性。这些结果表明,利用手性离子液体作为手性催化剂和手性介质,是一条绿色、经济的手性合成新途径。
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引用次数: 7
An Efficient, Clean, and Catalyst-Free Synthesis of Fused Pyrimidines Using Sonochemistry 一种高效、清洁、无催化剂的超声化学合成融合嘧啶
Pub Date : 2014-11-16 DOI: 10.1155/2014/406869
M. Mamaghani, K. Tabatabaeian, R. Araghi, A. Fallah, R. H. Nia
In this report, synthesis of indenopyrido[2,3-d]pyrimidine and pyrimido[4,5-b]quinoline derivatives was investigated via one-pot three-component reaction between 6-amino-2-(alkylthio)-pyrimidin-4(3H)one, 1,3-indanedione, or 1,3-cyclohexadione and arylaldehyde under ultrasonic irradiation in ethylene glycol as solvent at 65°C. In these reactions fused pyrimidine derivatives were synthesized with high to excellent yields (82–97%) and short reaction times (10–33 min).
本文研究了6-氨基-2-(烷基硫代)-嘧啶-4(3H) 1、1,3-茚二酮或1,3-环己二酮与芳醛在超声辐照下,在65℃下以乙二醇为溶剂进行一锅三组分反应,合成吲哚吡啶[2,3-]嘧啶和嘧啶[4,5-b]喹啉衍生物。在这些反应中合成了融合嘧啶衍生物,收率高(82-97%),反应时间短(10-33 min)。
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引用次数: 10
An Ultrasound Mediated Green Synthesis of Benzimidazolylthiounsaturatednitriles Using Water as a Green Solvent 超声介导的以水为绿色溶剂的苯并咪唑基硫不饱和腈的绿色合成
Pub Date : 2014-11-09 DOI: 10.1155/2014/403803
S. Rao, C. V. Reddy, P. Dubey
Reaction of 2-cyanothiomethylbenzimidazole  1 with an aromatic aldehydes in water under ultrasonic irradiation for 10–13 min gave the corresponding unsaturated nitriles 2a–h which is an efficient and simple method under green conditions. The unsaturated nitrile derivatives were obtained in 86–98% yield with a short reaction time without any tedious workup procedures.
2-氰硫甲基苯并咪唑1与芳香族醛在水中在超声波照射下反应10-13 min,得到相应的不饱和腈2a-h,这是绿色条件下一种高效、简便的方法。不饱和腈衍生物的收率为86-98%,反应时间短,无需繁琐的后处理程序。
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引用次数: 3
期刊
Organic Chemistry International
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