Synthesis and antitumor activity of optically active thiourea and their 2-aminobenzothiazole derivatives: a novel class of anticancer agents.

Manjula SN; Malleshappa Noolvi N; Vipan Parihar K; Manohara Reddy SA; Ramani V; Gadad AK; Singh G; Gopalan Kutty N; Mallikarjuna Rao C

首页> 外文期刊>European Journal of Medicinal Chemistry: Chimie Therapeutique >Synthesis and antitumor activity of optically active thiourea and their 2-aminobenzothiazole derivatives: a novel class of anticancer agents.

【24h】

Synthesis and antitumor activity of optically active thiourea and their 2-aminobenzothiazole derivatives: a novel class of anticancer agents.

机译：光学活性硫脲及其2-氨基苯并噻唑衍生物的合成及其抗肿瘤活性：一类新型的抗癌药。

获取原文

获取原文并翻译 | 示例

掌桥外文数据库（机构版） >>

开具论文收录证明 >>

文献代查 >>

页面导航

摘要
著录项
相似文献
相关主题

摘要

A novel series of optically active 2-aminobenzothiazole derivatives were synthesized by reaction of optically active amine (I) with thiophosgene to obtain optically active isothiocyanates (IIa-h) which on condensation with 4-fluoro-3-chloro aniline (III) yielded various optically active thioureas (IVa-h). Further oxidative cyclisation in the presence of bromine and chloroform yielded title compounds (Va-h). The structures of these compounds were established by IR, (1)H NMR, (13)C NMR, Mass and HRMS. The compounds (IVa-h and Va-h) were evaluated for in vitro cytotoxicity against mouse Ehrlich Ascites Carcinoma (EAC) and two human cancer cell lines (MCF-7 and HeLa). In preliminary MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] cytotoxicity studies the optically active thiourea derivatives (IVe, IVf and IVh) were found most effective. In EAC cells the IC(50) values for IVe, IVf, IVh and Vg were found in the range of 10-24 microM, whereas in MCF-7 and HeLa cells the IC(50) values were observed in the range of 15-30 microM and 33-48 microM, respectively. In alkaline comet assay the compounds (IVe and IVf) showed dose-dependent DNA damaging activity.

机译：通过光学活性胺（I）与硫光气反应合成了一系列新型的光学活性2-氨基苯并噻唑衍生物，获得了光学活性异硫氰酸酯（IIa-h），其与4-氟-3-氯苯胺（III）缩合得到各种旋光硫脲（IVa-h）。在溴和氯仿的存在下进一步的氧化环化产生标题化合物（Va-h）。这些化合物的结构通过IR，（1）H NMR，（13）C NMR，质量和HRMS确定。评价了化合物（IVa-h和Va-h）对小鼠艾氏腹水癌（EAC）和两种人类癌细胞系（MCF-7和HeLa）的体外细胞毒性。在初步的MTT [3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物]细胞毒性研究中，发现旋光性硫脲衍生物（IVe，IVf和IVh）最有效。在EAC细胞中，IVe，IVf，IVh和Vg的IC（50）值在10-24 microM范围内，而在MCF-7和HeLa细胞中，观察到的IC（50）值在15-microM范围内。 30 microM和33-48 microM。在碱性彗星试验中，化合物（IVe和IVf）显示出剂量依赖性的DNA破坏活性。

著录项

来源
《European Journal of Medicinal Chemistry: Chimie Therapeutique》 |2009年第7期|共7页
作者
Manjula SN; Malleshappa Noolvi N; Vipan Parihar K; Manohara Reddy SA; Ramani V; Gadad AK; Singh G; Gopalan Kutty N; Mallikarjuna Rao C;
展开▼
作者单位

展开▼
收录信息
原文格式 PDF
正文语种 eng
中图分类药学;
关键词

相似文献

外文文献
中文文献
专利

1. Synthesis and antitumor activity of optically active thiourea and their 2-aminobenzothiazole derivatives: a novel class of anticancer agents. [J] . Manjula SN, Malleshappa Noolvi N, Vipan Parihar K, European Journal of Medicinal Chemistry: Chimie Therapeutique . 2009,第7期

机译：光学活性硫脲及其2-氨基苯并噻唑衍生物的合成及其抗肿瘤活性：一类新型的抗癌药。
2. Antitumor agents 251: Synthesis, cytotoxic evaluation, and structure-activity relationship studies of phenanthrene-based tylophorine derivatives (PBTs) as a new class of antitumor agents. [J] . Wei L, Brossi A, Kendall R, Bioorganic and Medicinal Chemistry . 2006,第19期

机译：抗肿瘤剂251：作为新型抗肿瘤剂的基于菲的酪氨酸衍生物（PBT）的合成，细胞毒性评估和构效关系研究。
3. Synthesis and antiproliferative activity of benzocyclobutacarbazol derivatives. A new class of potential antitumor agents. [J] . Graf-Christophe S, Kuehm-Caubere C, Renard P, Bioorganic and Medicinal Chemistry Letters . 2000,第23期

机译：苯并环丁卡巴唑衍生物的合成及其抗增殖活性。一类新的潜在抗肿瘤药。
4. Synthesis and toxicological activity of 5-nitroindazole sulfonamides derivatives as potential antimicrobial agents. Optimization of the synthesis [C] . Corina Cheptea, Andreea-Celia Benchea, Marius Găină, 2017 E-Health and Bioengineering Conference . 2017

机译：5-硝基吲唑磺酰胺衍生物作为潜在抗菌剂的合成及其毒理活性。优化合成
5. Part One. Synthesis of optically active tryptophan derivatives with potential activity as indoleamine 2,3-dioxygenase inhibitors: An approach via asymmetric catalytic hydrogenation. Part Two. Design, synthesis and pharmacology of selective ligands for alpha1-containing GABA(A)/benzodiazepine receptor subtypes: SAR studies of beta-carbolines at positions -3 and -6 and their corresponding bivalent ligands. Part Three. First enantiospecific total synthesis of the important biogenetic intermediates, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epi-vellosimine and macusine A. [D] . Yin, Wenyuan. 2007

机译：第一部分。具有吲哚胺2,3-二加氧酶抑制剂潜在活性的旋光色氨酸衍生物的合成：一种通过不对称催化氢化的方法。第二部分。含α1的GABA（A）/苯并二氮杂receptor受体亚型的选择性配体的设计，合成和药理作用：位于-3和-6位的β-咔啉及其相应的二价配体的SAR研究。第三部分。重要生物遗传中间体，（+）-聚神经氨酸和（+）-聚神经氨酸醛，以及16-表-维西辛和Macusine A的首次对映体全合成。
6. Antimicrobial and anticancer activity of some novel fluorinated thiourea derivatives carrying sulfonamide moieties: synthesis biological evaluation and molecular docking [O] . Mostafa M. Ghorab, Mansour S. Alsaid, Mohamed S. A. El-Gaby, 2017

机译：某些带有磺酰胺基团的新型氟化硫脲衍生物的抗菌和抗癌活性：合成生物学评估和分子对接
7. Studies on 2(1H)-quinolinone derivatives as gastric antiulcer active agents. Synthesis and antiulcer activities of optically active .ALPHA.-amino acid derivatives of 2(1H)-quinolinone and oxindole. [O] . MINORU UCHIDA, FUJIO TABUSA, MAKOTO KOMATSU, 1987

机译：研究2（1H）-Quinolinone衍生物作为胃浸活性剂。光学活性型。 - α-氨基酸衍生物的合成及抗腐殖活性为2（1H） - 喹啉酮和氧吲哚。
8. Synthesis and Biological Activity of Substituted Urea and Thiourea Derivatives Containing 1,2,4-Triazole Moieties. [R] . Kocyigit-Kaymakcioglu, B., Celen, A. O., Tabanca, N., 2013

机译：含1,2,4-三唑部分的取代脲和硫脲衍生物的合成及生物活性。

Synthesis and antitumor activity of optically active thiourea and their 2-aminobenzothiazole derivatives: a novel class of anticancer agents.

摘要

著录项

相似文献

相关主题

期刊订阅