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Newly designed organotin(IV) carboxylates with peptide linkage: Synthesis, structural elucidation, physicochemical characterizations and pharmacological investigations
European Journal of Medicinal Chemistry ( IF 6.7 ) Pub Date : 2017-11-04 , DOI: 10.1016/j.ejmech.2017.11.001
Muhammad Sirajuddin , Vickie McKee , Muhammad Tariq , Saqib Ali

Fourteen new organotin(IV) carboxylate complexes with peptide linkage of (2-(4-methoxy-2-nitrophenylcarbamoyl)benzoic acid) were successfully synthesized and characterized by elemental analyses, FT-IR, NMR (1H, 13C and 119Sn) and single crystal X-ray techniques. FT-IR results of the sodium salt of 2-(4-methoxy-2-nitrophenylcarbamoyl)benzoic acid and complexes showed that the coordination took place via oxygen atoms of the carboxylate group. 1J(119Sn-13C), 2J(119Sn-1H) and θ values calculated from 1H and 13C NMR data using Lockhart's equation reveal a trigonal bipyramidal geometry for triorganotin(IV) derivatives and an octahedral geometry for diorganotin(IV) derivatives. Crystallographic data for three triorganotin(IV) complexes (13) showed the tin has distorted trigonal bipyramidal geometry. In vitro anticancer activity against lung carcinoma (H-157) and kidney fibroblast (BHK-21) cell lines as well as antileishmanial activity against the promastigote forms of leishmania major of the synthesized compounds were also studied and the complexes were found biologically active. The in vitro antibacterial activity of most of the synthesized organotin(IV) derivatives against the studied bacterial pathogens is higher than those of the standard 3rd generation antibiotics such as Tetracycline, Penicillin G, Ampicillin, Amoxicillin. This suggest the use of these newly designed organotin(IV) derivatives as potent antibiotics. The synthesized compounds interact with DNA via intercalative mode of interaction. Viscosity measurement results also support the intercalative mode of interaction for the compounds with DNA.



中文翻译:

新型设计的具有肽键的有机锡(IV)羧酸盐:合成,结构阐明,理化特性和药理研究

成功合成了14种具有(2-(4-甲氧基-2-硝基苯基氨基甲酰基)苯甲酸的肽键的有机锡(IV)羧酸酯配合物,并通过元素分析,FT-IR,NMR(1 H,13 C和119 Sn )和单晶X射线技术。的2-(4-甲氧基-2- nitrophenylcarbamoyl)的钠盐的FT-IR结果苯甲酸和络合物表明,协调发生经由羧酸基团的氧原子。1 J119 Sn- 13 C),2 J119 Sn- 1 H)和从1 H和13计算出的θ值使用Lockhart方程的C NMR数据揭示了三有机锡(IV)衍生物的三角双锥体几何形状和双有机锡(IV)衍生物的八面体几何形状。三个三有机锡(IV)配合物(晶体学数据1 - 3)显示锡已经扭曲三角双锥几何形状。还研究了合成化合物对肺癌(H-157)和肾成纤维细胞(BHK-21)细胞系的体外抗癌活性以及对利什曼原虫主要前鞭毛体形式的抗疟疾活性,并且发现该复合物具有生物活性。在体外大多数合成的有机锡(IV)衍生物对所研究的细菌病原体的抗菌活性均高于标准的第三代抗生素,如四环素,青霉素G,氨苄青霉素,阿莫西林。这表明使用这些新设计的有机锡(IV)衍生物作为有效的抗生素。合成的化合物通过相互作用的嵌入模式与DNA相互作用。粘度测量结果还支持化合物与DNA相互作用的插入模式。

更新日期:2017-11-04
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