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Synthesis, characterization and biological evaluation of some novel sulfonylthiosemicarbazides 几种新型磺基硫代氨基脲的合成、表征及生物学评价
Pub Date : 2019-07-01 DOI: 10.1080/10426507.2019.1633320
Sevil Şenkardeş, I. Han, H. Hançer, Mürüvvet Abbak, Ö. Çevik, Ş. Güniz Küçükgüzel
Abstract A series of thiosemicarbazides were synthesized and structurally characterized by spectroscopic techniques (NMR, FT-IR) besides elemental analysis. These compounds were evaluated for their cytotoxicity against human breast cancer cell line MCF7 and prostate cancer cell line PC3 and nonmalignant fibroblast L929 cell line by MTT assay. Among the compounds, N-[2-(4-chlorophenyl)ethyl]-2-[(4-methylphenyl)sulfonyl]hydrazinecarbothioamide (3d) and 2-[(4-methylphenyl)sulfonyl]-N-[4-(trifluoromethoxy)phenyl]hydrazinecarbothioamide (3f) were found to display significant cytotoxicity with IC50 of 13.87 μM (against PC3 cell line) and 1.47 μM (against MCF7 cell line), respectively. These compounds were non-cytotoxic to normal cell line with IC50>100 μM. Western blotting studies demonstrated that compound 3f induced apoptosis and caused cell death in the MCF7 and PC3 cell lines via an increase in Bax protein expression and a slight decrease in Bcl-2 protein expression. The gene expression ratio Bax/Bcl-2 showed the induction of mitochondrial apoptosis in cancer cell lines. All of synthesized compounds have also been tested for antioxidant activity and all compounds achieved strong inhibition of the DPPH radical. These findings showed that compound 3f, displays potential to be further explored in the development of new anticancer agents. Graphical Abstract
摘要合成了一系列硫代氨基脲类化合物,并采用NMR、FT-IR等光谱技术对其进行了结构表征。用MTT法评价了这些化合物对人乳腺癌细胞系MCF7、前列腺癌细胞系PC3和非恶性成纤维细胞L929的细胞毒性。其中,N-[2-(4-氯苯基)乙基]-2-[(4-甲基苯基)磺酰基]hydrazinecarbothioamide (3d)和2-[(4-甲基苯基)磺酰基]-N-[4-(三氟甲氧基)苯基]hydrazinecarbothioamide (3f)对PC3细胞株和MCF7细胞株分别具有显著的细胞毒性,IC50分别为13.87 μM和1.47 μM。这些化合物在IC50 ~ 100 μM范围内对正常细胞系无细胞毒性。Western blotting研究表明,化合物3f通过增加Bax蛋白表达,轻微降低Bcl-2蛋白表达,诱导MCF7和PC3细胞系细胞凋亡,导致细胞死亡。基因表达比Bax/Bcl-2显示诱导癌细胞线粒体凋亡。所有合成的化合物都进行了抗氧化活性测试,所有化合物都对DPPH自由基有很强的抑制作用。这些发现表明,化合物3f在开发新的抗癌药物方面具有进一步探索的潜力。图形抽象
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引用次数: 2
Recent trends in the synthesis of 1,2,3-thiadiazoles 1,2,3-噻二唑合成的最新进展
Pub Date : 2019-06-28 DOI: 10.1080/10426507.2019.1633323
Ali Irfan, Fozia Batool, Sajjad Ahmad, R. Ullah, Aeysha Sultan, R. Sattar, Bushra Nisar, Laila Rubab
Abstract 1,2,3-Thiadiazoles, structurally active pharmacophores have attracted significant attention of synthetic chemists, medicinal and pharmaceutical researchers because of their versatile biological activities against various diseases such as herbicidal, insecticidal, antiviral, antitumor, antimicrobial, anticancer, plants activator and anti-amoebic activities. A literature survey of the last decade presented in this review article summarizes the major synthetic approaches, methodologies and strategies adopted for the synthesis of 1,2,3-thiadiazole scaffolds which will be help for medicinal chemists and pharmacists in future synthesis and development of novel therapeutic agents. Graphical Abstract
摘要1,2,3-噻二唑类结构活性药物因其具有除草、杀虫、抗病毒、抗肿瘤、抗菌、抗癌、植物激活剂和抗阿米巴等多种生物活性而受到合成化学家和药学研究者的广泛关注。本文综述了近十年来国内外有关1,2,3-噻二唑类支架的主要合成途径、方法和策略,为药物化学家和药剂师今后合成和开发新型治疗药物提供参考。图形抽象
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引用次数: 3
Synthesis and cytotoxicity of new 2-oxo-7-phenyl-2,3-dihydrothiazolo[4,5-b]pyridine-5-carboxylic acid amides 新型2-氧-7-苯基-2,3-二氢噻唑[4,5-b]吡啶-5-羧酸酰胺的合成及细胞毒性研究
Pub Date : 2019-06-27 DOI: 10.1080/10426507.2019.1633318
A. Lozynskyi, B. Zimenkovsky, I. Ivasechko, J. Senkiv, A. Gzella, O. Karpenko, R. Stoika, R. Lesyk
Abstract The synthesis and anticancer activity evaluation of new thiazolo[4,5-b]pyridine-5-carboxylic acid amides is described. The structures of the synthesized compounds were confirmed by spectroscopic data and a single crystal X-ray diffraction analysis for 2.4. The synthesized compounds were screened for their in vitro anticancer activity according to US NCI protocols. The most active 7-(4-fluorophenyl)-2-oxo-2,3-dihydrothiazolo[4,5-b]pyridine-5-carboxylic acid (4-chlorophenyl)amide 2.2 and 7-(4-chlorophenyl)-2-oxo-2,3-dihydrothiazolo[4,5-b]pyridine-5-carboxylic acid (4-chlorophenyl)amide 2.5 were screened for their cytotoxicity effects on C6 Rat glioma cells and U373 Human glioblastoma astrocytoma cells which revealed promising results comparable to temozolamide as reference control according MTT assay data. GRAPHICAL ABSTRACT
摘要本文报道了新型噻唑类[4,5-b]吡啶-5-羧酸酰胺的合成及其抗癌活性评价。通过光谱数据和单晶x射线衍射分析证实了合成化合物的结构。根据美国NCI方案对合成的化合物进行体外抗癌活性筛选。筛选活性最高的7-(4-氟苯基)-2-氧-2,3-二氢噻唑[4,5-b]吡啶-5-羧酸(4-氯苯基)酰胺2.2和7-(4-氯苯基)-2-氧-2,3-二氢噻唑[4,5-b]吡啶-5-羧酸(4-氯苯基)酰胺2.5对C6大鼠胶质瘤细胞和U373人胶质母细胞瘤星形细胞瘤细胞的细胞毒性作用,结果显示与替莫唑胺作为对照的效果相当。图形抽象
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引用次数: 4
Design, synthesis and herbicidal activity of novel cyclic phosphonates with diaryl ethers containing pyrimidine 新型含嘧啶二芳醚环膦酸盐的设计、合成及其除草活性
Pub Date : 2019-06-27 DOI: 10.1080/10426507.2019.1633319
Shasha Zhang, X. Guo, Yuan Zhou, Yalan Yang, Hao Peng, H. He
Abstract Thirteen novel cyclic phosphates were rationally designed and synthesized by introducing diary ethers containing pyrimidine. All the target compounds were characterized by 1H, 13C, 31P NMR and HRMS. The test of herbicidal activity indicated that most of the compounds showed good herbicidal activities against Amaranthus retroflexus. The compounds IA-2 (1-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)propyl-2-((4,6-dimethoxypyrimidin-2-yl)oxy)benzoate) and IA-3 ((5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)(phenyl)methyl-2-((4,6-dimethoxypyrimidin-2-yl)oxy)benzoate) exhibited remarkable post-emergency herbicidal activity against the tested monocotyledonous weed at the dosage of 112.5 g ai/ha. Graphical Abstract
摘要通过引入含嘧啶的日记醚,合理设计合成了13种新型环状磷酸盐。所有目标化合物均通过1H、13C、31P NMR和HRMS进行了表征。除草活性试验表明,大部分化合物对红苋菜具有良好的除草活性。化合物IA-2(1-(5,5-二甲基-2-氧化-1,3,2-二氧磷-2-基)丙基-2-((4,6-二甲氧磷-2-基)氧)苯甲酸酯)和IA-3((5,5-二甲基-2-氧化-1,3,2-二氧磷-2-基)苯基)甲基-2-((4,6-二甲氧磷-2-基)苯甲酸酯)在112.5 g /ha剂量下对单子叶杂草表现出显著的灾后除草活性。图形抽象
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引用次数: 3
CeCl3⋅7H2O-catalysed hydrophosphonylation of aldehydes and ketones: An expeditious route to α-hydroxyphosphonates under solvent-free conditions CeCl3·7h2o催化醛和酮的氢膦化:无溶剂条件下α-羟基膦酸盐的快速途径
Pub Date : 2019-06-26 DOI: 10.1080/10426507.2019.1633532
R. Mahesh, Rupali Sharma, P. Kour, Anil Kumar
Abstract A cerium(III) chloride-catalysed expeditious synthesis of α-hydroxyphosphonates via a modified Abramov synthetic protocol has been developed. The scope of the current protocol is broad, with a range of aromatic, α,β-unsaturated and heterocyclic aldehydes being efficiently converted to the anticipated products in very good to excellent yields (89–96%) in 15 min using low catalytic loading. The protocol was efficiently extended to hitherto unactivated cyclic ketones such as cyclopentanone and cyclohexanone to afford the required products in excellent yields. However, the reaction with cyclohexenone delivered a Michael product instead of the anticipated α-hydroxyphosphonates. The solvent-free conditions, low catalytic loadings, avoidance of toxic reagents and good to excellent yields are significant advantages of this protocol. Graphical Abstract
摘要采用改进的阿布拉莫夫合成工艺,制备了氯化铈催化快速合成α-羟基膦酸盐的方法。目前的方案范围很广,在低催化负荷的情况下,芳香族、α、β-不饱和醛和杂环醛在15分钟内以非常好的收率(89-96%)有效地转化为预期的产品。该方案有效地扩展到迄今未活化的环酮,如环戊酮和环己酮,以高收率提供所需的产品。然而,与环己酮的反应产生了Michael产物,而不是预期的α-羟基膦酸盐。无溶剂条件,低催化负荷,避免有毒试剂和良好的收率是该方案的显著优点。图形抽象
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引用次数: 2
Synthesis, characterization, structural elucidation and biological screening of some bis(diisobutyldithiophosphato)antimony(III) complexes 一些双(二异丁基二硫代磷酸)锑(III)配合物的合成、表征、结构解析和生物学筛选
Pub Date : 2019-06-24 DOI: 10.1080/10426507.2019.1618300
H. Chauhan, Nitin Carpenter, S. Bhatiya, S. Joshi
Abstract Seven complexes of type [(C4H9i-O)2PS2]2SbR have been synthesized by the reaction of chlorobis(diisobutyldithiophosphato)antimony(III) with mixed thio and/or oxo donor ligands in 1:1 M stoichiometry, where R = SC6H5, OOCC6H5, SCH2COOH, SOCCH3, OOCCH3, SC6H4COOH and OOC(OH)C6H4. These newly synthesized derivatives have been characterized by different physicochemical (elemental analysis (C, H, S, Sb), melting point, molecular weight determination), spectral (UV, IR, NMR (1H, 13C and 31P)) studies, as well as ESI mass, thermal, powder XRD and biological studies. In the final step of weight loss in thermogravimetric analysis, occurring in the range of 245–505 °C, the degradation of the C6H3CO moieties takes place and antimony sulfide (1/2 Sb2S3) is obtained as remaining material, which is useful in various aspects. Bonded to antimony the diisobutyldithiophosphato substituent behaves as an anisobidentate ligand, which is confirmed through spectral analysis. Powder XRD studies indicate that these compounds crystallize in a monoclinic crystal system with an unit cell volume of ∼7074–7162 Å3 forming nano ranged (9.69–15.69 nm) crystallites. From the antimicrobial screening tests, bis(diisobutyldithiophosphato)antimony(III) thioglycolate (compound 3) has shown a maximum zone of inhibition (19 mm) against E. coli at 200 μg mL−1 concentration. Graphical Abstract
摘要以氯(二异丁基二硫代磷酸)锑(III)与硫和/或氧混合配体按1:1 M的化学计量法合成了七种[(C4H9i-O)2PS2]2SbR配合物,其中R = SC6H5、OOCC6H5、SCH2COOH、SOCCH3、OOCCH3、SC6H4COOH和OOC(OH)C6H4。这些新合成的衍生物已经通过不同的物理化学(元素分析(C, H, S, Sb),熔点,分子量测定),光谱(UV, IR, NMR (1H, 13C和31P))研究以及ESI质量,热,粉末XRD和生物学研究进行了表征。在热重分析失重的最后一步,在245-505℃范围内,发生C6H3CO部分的降解,得到硫化锑(1/2 Sb2S3)作为剩余物质,它在许多方面都是有用的。二异丁基二硫代磷取代基与锑结合,表现为异齿配体,通过光谱分析证实了这一点。粉末XRD研究表明,这些化合物在单斜晶系中结晶,单位晶胞体积为~ 7074-7162 Å3,形成纳米范围(9.69-15.69 nm)的晶体。从抗菌筛选试验中,双(二异丁基二硫代磷酸酯)锑(III)巯基乙酸盐(化合物3)在200 μg mL−1浓度下对大肠杆菌有最大抑制区(19 mm)。图形抽象
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引用次数: 1
Foreword for the special issue of phosphorus, sulfur, and silicon and the related elements dedicated to ICPC 22 – 2018 icpc22 - 2018磷、硫、硅及相关元素专刊前言
Pub Date : 2019-05-27 DOI: 10.1080/10426507.2019.1627057
G. Keglevich
I am happy to introduce this special issue of Phosphorus, Sulfur, and Silicon and the Related Elements, which presents voluntarily submitted papers from the 22 International Conference on Phosphorus Chemistry (www.icpc22.mke.org. hu) held in Budapest, Hungary from 8–13 July 2018. The venue for the conference was the Hotel Flamenco located in the heart of the Buda part of Budapest (Figure 1). It was a great honor for us, as Hungarian organophosphorus chemists, to have the pleasure of organizing this prestigious event in Hungary. ICPCs are always highly-ranked events held in the past every 3 years, and biannually, more recently. Prestigious gatherings, such as this one remain in great demand, and represent a continuum of high quality during a time when we receive many invitations to predatory conferences. ICPCs are indeed different kinds of events. My first such conference was the 10 ICPC in Bonn organized by
我很高兴地介绍这一期《磷、硫、硅和相关元素》特刊,它介绍了第22届国际磷化学会议(www.icpc22.mke.org)上自愿提交的论文。2018年7月8日至13日在匈牙利布达佩斯举行。会议地点是位于布达佩斯布达中心的弗拉门戈酒店(图1)。作为匈牙利有机磷化学家,我们非常荣幸能够在匈牙利组织这次享有盛誉的活动。国际会议一直是高级别活动,过去每三年举行一次,最近每两年举行一次。在我们收到许多掠夺性会议的邀请之际,像这次这样的著名会议仍然需求量很大,代表着高质量的连续统一体。ICPCs确实是不同类型的事件。我第一次参加这样的会议是在波恩召开的ICPC大会
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引用次数: 0
Foreword for international conference on phosphorus chemistry – ICPC 22 第22届国际磷化学会议前言
Pub Date : 2019-05-27 DOI: 10.1080/10426507.2019.1627055
M. Rudd
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引用次数: 0
Dimethylsulfoxide-induced trinuclear Co(II) and Ni(II) salamo-type complexes: Syntheses, crystal structures and spectral properties 二甲基亚砜诱导的三核Co(II)和Ni(II) salamo型配合物:合成、晶体结构和光谱性质
Pub Date : 2018-04-19 DOI: 10.1080/10426507.2018.1452228
Xiao-yan Li, Q. Kang, Qing-Qing Zhao, Jian-Chun Ma, W. Dong
GRAPHICAL ABSTRACT ABSTRACT Two homotrinuclear Co(II) and Ni(II) complexes, [{CoL(OAc)(DMSO)}2Co]·2DMSO and [{NiL(OAc)(DMSO)}2Ni] have been synthesized by the reaction of 4,4′-dichloro-2,2′-[(1,3-propylene)dioxybis(nitrilomethylidyne)]diphenol (H2L) with cobalt(II) and nickel(II) acetate tetrahydrate in the solution of DMSO, respectively, and characterized by elemental analyses, IR, UV–Vis spectra and X-ray crystallography. In the Co(II) complex, terminal Co2 and Co2#1 atoms located in the N2O2 sites, and are both hexa-coordinated with slightly distorted octahedral geometries. While the central Co1 atom is also hexa-coordinated by six oxygen atoms, four are phenoxy oxygen atoms from two (L)2− units, and two oxygen atoms from µ2-acetate ions, which has formed a octahedral geometry. In the Ni(II) complex, coordination environments of the Ni(II) atoms are similar to those of the Co(II) atoms. Infinite 1D supramolecular structure is formed via abundant intermolecular hydrogen bonding interactions in the Co(II) complex.
摘要在DMSO溶液中,以4,4′-二氯-2,2′-[(1,3-丙烯)二氧双(硝基甲基炔)]双酚(H2L)与四水合钴(II)和四水合乙酸镍(II)为原料,合成了[{CoL(OAc)(DMSO)}2Co]·2DMSO和[{NiL(OAc)(DMSO)}2Ni]两个同核Co(II)和Ni(II)配合物,并用元素分析、IR、UV-Vis光谱和x射线晶体学对其进行了表征。在Co(II)配合物中,末端Co2和Co2#1原子位于N2O2位点,并且都是六配位的,具有轻微扭曲的八面体几何形状。中心的Co1原子也由6个氧原子六配位,其中4个是来自2 (L)2 -单元的苯氧氧原子,2个是来自µ2-乙酸离子的氧原子,形成了八面体结构。在Ni(II)配合物中,Ni(II)原子的配位环境与Co(II)原子的配位环境相似。Co(II)配合物通过丰富的分子间氢键相互作用形成无限一维超分子结构。
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引用次数: 3
A domino knoevenagel-phospha-michael reaction: One-pot synthesis of novel organophosphonates in the presence of multi-walled carbon nanotube‒CO‒NH(CH2)2NH-SO3H as catalyst 多壁碳纳米管co - nh (CH2)2NH-SO3H催化下,一锅合成新型有机膦酸盐
Pub Date : 2018-04-18 DOI: 10.1080/10426507.2018.1452230
Fatemeh Homayoun, Soheila Ghassamipour
GRAPHICAL ABSTRACT ABSTRACT We report a one-pot method for the synthesis of various substituted 1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl phosphonate derivatives via phosphorus-carbon bond formation through domino Knoevenagel–phospha–Michael reaction. Multi-walled carbon nanotube‒CO‒NH(CH2)2NH-SO3H was used as an acidic heterogeneous catalyst. The catalyst could be used four times without losing its catalytic activity. The structures of the products were determined by FT-IR spectra, 1H-, 13C- and 31P- Nuclear Magnetic Resonance and elemental analysis. Recovery and reusability of catalyst, simplicity, applicability, good reaction time and good yields of products are the benefits of this work.
摘要本文报道了通过多米诺Knoevenagel-phospha-Michael反应形成磷碳键,一锅法合成了各种取代的1,3-二甲基-2,4,6-三氧六氢嘧啶-5-酰基膦酸盐衍生物。采用多壁碳纳米管co - nh (CH2)2NH-SO3H作为酸性非均相催化剂。该催化剂可重复使用四次而不失去催化活性。通过FT-IR、1H-、13C-、31P-核磁共振和元素分析对产物的结构进行了表征。催化剂的回收和可重复使用、简单、适用性强、反应时间短、产品收率高是本研究的优点。
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引用次数: 2
期刊
Phosphorus Sulfur and Silicon and The Related Elements
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