N-(1,3-苯并噻唑-2-基)-2-氯乙酰胺 | 3028-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: N-(1,3-苯并噻唑-2-基)-2-氯乙酰胺
• 中文别名: N-(1,3-苯并噻唑-2-基)-2-氯-乙酰胺
• 英文名称: N-benzothiazol-2-yl-2-chloroacetamide
• 英文别名: N-(benzo[d]thiazol-2-yl)-2-chloroacetamide；N-(1,3-benzothiazol-2-yl)-2-chloroacetamide；N-benzothiazolyl-2-chloroacetamide；2-chloroacetylamino benzothiazole；2-chloro-N-(benzo[d]thiazol-2-yl)acetamide；N-(1,3-benzothiazole-2-yl)-2-chloroacetamide；2-Chloracetylamino-benzothiazol；2-Chloracetylamino-benzthiazol
• CAS: 3028-02-2
• 化学式: C₉H₇ClN₂OS
• mdl: MFCD00022860
• 分子量: 226.686
• InChiKey: CMUZFXFDVGLPGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  N-(1,3-苯并噻唑-2-基)-2-氯乙酰胺 在 肼 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 以72%的产率得到N-2-苯并噻唑基-2-肼基-乙酰胺
  参考文献：
  名称：

  Srivastava; Sen, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 10, p. 1583 - 1586

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基硫脲 在 溴 、 溶剂黄146 、 三乙胺 作用下， 以 苯 为溶剂， 反应 10.0h， 生成 N-(1,3-苯并噻唑-2-基)-2-氯乙酰胺
  参考文献：
  名称：

  Kumar, Arun; Shakya, Ashok K.; Siddiqui, Indian Journal of Heterocyclic Chemistry, 2016, vol. 25, # 3-4, p. 243 - 249

  摘要：

  DOI：

文献信息

• 2-(3,4-Dihydro-4-Oxothieno[2,3-d]pyrimidin-2-ylthio) Acetamides as a New Class of Falcipain-2 Inhibitors. 3. Design, Synthesis and Biological Evaluation
  作者：Jin Zhu、Tong Chen、Jie Liu、Ruoqun Ma、Weiqiang Lu、Jin Huang、Honglin Li、Jian Li、Hualiang Jiang

  DOI：10.3390/molecules14020785

  日期：——

  The cysteine protease falcipain-2 (FP-2) of Plasmodium falciparum is a principal cysteine protease and an essential hemoglobinase of erythrocytic P. falciparum trophozoites, making it become an attractive target enzyme for developing anti-malarial drugs. In this study, a series of novel small molecule FP-2 inhibitors have been designed and synthesized based on compound 1, which was identified by using structure-based virtual screening in conjunction with an enzyme inhibition assay. All compounds showed high inhibitory effect against FP-2 with IC50s of 1.46-11.38 μM, and the inhibitory activity of compound 2a was ~2 times greater than that of prototype compound 1. The preliminary SARs are summarized and should be helpful for future inhibitor design, and the novel scaffold presented here, with its potent inhibitory activity against FP-2, also has potential application in discovery of new anti-malarial drugs.

  恶性疟原虫 (Plasmodium falciparum) 半胱氨酸蛋白酶 (falcipain-2， FP-2) 是原生质型疟原虫的主要半胱氨酸蛋白酶和必须的血红蛋白酶，这使得它成为研制抗疟药物的一个有吸引力的靶标酶。在本研究中，我们基于用酶抑制法结合基于结构的虚拟筛选得到的化合物 1，设计并合成了系列新型小分子 FP-2 抑制剂。所有化合物均为 FP-2的高效抑制剂，其半抑制浓度 (IC50) 值范围为 1.46 至 11.38 μM，化合物 2a 的抑制活性是母体化合物 1 的 2倍左右。本研究概括总结的初步构效关系将有助于未来抑制剂的设计，这里展示的新骨架以其对 FP-2的强效抑制活性，在发现新型抗疟药物方面也具有潜在的应用价值。
• Synthesis and Biological Evaluation of some Amide Derivatives Bearing Benzothiazole and Piperidine Moieties as Antimicrobial Agents
  作者：Mehlika Dilek Altintop、Ahmet Ozdemir、Zafer Asim Kaplancikli、Gulhan Turan-Zitouni、Gokalp Iscan、Gulsen Akalin Ciftci

  DOI：10.2174/1570180811310050013

  日期：2013.4.1

  In this study, N-(benzothiazol-2-yl)-2-(piperidin-1-yl)acetamide derivatives (1-24) were obtained by the reaction of 2-chloro-N-(benzothiazole-2-yl)acetamides with piperidine derivatives. The structures of the compounds were elucidated by 1H-NMR and mass spectral data and elemental analysis. The compounds were screened for their antimicrobial activities against pathogenic bacteria and Candida species. The compounds were also investigated for their cytotoxic properties using MTT assay. The microbiological results revealed that the compounds were more effective against fungi than bacteria. Among Candida species, C. utilis was the most susceptible fungus to compounds 7 and 11. It is apparent that 2,6-dimethylpiperidine group and chloro and methyl substituents on benzothiazole ring have an important impact on anticandidal activity. MTT assay indicated that the effective doses of these derivatives were lower than their cytotoxic doses.

  在本研究中，通过2-氯-N-(苯并噻唑-2-基)乙酰胺与哌啶衍生物的反应，合成了N-(苯并噻唑-2-基)-2-(哌啶-1-基)乙酰胺衍生物(1-24)。通过1H-NMR、质谱数据和元素分析阐明了化合物的结构。筛选了这些化合物对病原菌和念珠菌的抗微生物活性。还利用MTT法研究了它们的细胞毒性。微生物学结果显示，这些化合物对真菌的活性强于细菌。在念珠菌属中，对化合物7和11，新型隐球酵母最为敏感。显然，哌啶环上的2,6-二甲基及苯并噻唑环上的氯和甲基取代基对杀念珠菌活性具有重要作用。MTT法结果表明，这些衍生物的有效剂量低于其细胞毒剂量。
• Synthesis and biological evaluation of N-(substituted phenyl)-2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfanyl)acetamides as antimicrobial, antidepressant, and anticonvulsant agents
  作者：N. Shruthi、Boja Poojary、Vasantha Kumar、A. Prathibha、Mumtaz Mohammed Hussain、B. C. Revanasiddappa、Himanshu Joshi

  DOI：10.1134/s1068162015020144

  日期：2015.3

  N-Aryl-2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfanyl)acetamides were synthesized by condensation of tricyclic compound 2,5-dihydro-3H-[1,2,4]triazino[5,6-b]indole-3-thione with chloro N-phenylacetamides. The tricyclic compound was obtained by condensation of Isatin with thiosemicarbazide. Chloro N-phenylacetamides were obtained from different substituted anilines. Their structures were characterized by

  通过三环化合物2,5-二氢-3H-缩合合成了一系列新的N-Aryl-2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfanyl)乙酰胺[1,2,4]triazino[5,6-b]indole-3-thione 与氯 N-苯基乙酰胺。三环化合物是由靛红与氨基硫脲缩合得到的。氯 N-苯基乙酰胺是从不同的取代苯胺中获得的。它们的结构通过IR、1H NMR、LC-MS和元素分析表征。筛选新合成的化合物的抗微生物、抗抑郁和抗惊厥活性。初步结果表明，当测试抗微生物活性时，大多数化合物的 MIC 值低于使用的标准药物。一些化合物具有非常好的抗抑郁和抗惊厥活性。
• Design and Synthesis of New 1,3,4-Oxadiazole – Benzothiazole and Hydrazone Derivatives as Promising Chemotherapeutic Agents
  作者：Betül Kaya、Weiam Hussin、Leyla Yurttaş、Gülhan Turan-Zitouni、Hülya Gençer、Merve Baysal、Abdullah Karaduman、Zafer Kaplancıklı

  DOI：10.1055/s-0042-119070

  日期：2017.5

  Looking for new cytotoxic and antimicrobial agents with improved antitumor activity, a series of hydrazide and oxadiazole derivatives were designed and synthesized using 3-methoxyphenol as starting substance. Novel N'-(arylidene)-2-(3-methoxyphenoxy)acetohydrazide derivatives (4a-f)/1-(4-substitutedphenyl)-2-[(5-[(3-methoxyphenoxy)methyl]-1,3,4-oxadiazol-2-yl)thio]ethan-1-one derivatives (6a-f)/N-

  为了寻找具有改善的抗肿瘤活性的新的细胞毒性和抗菌剂，以3-甲氧基苯酚为起始原料设计并合成了一系列酰肼和恶二唑衍生物。新的N'-（亚芳基）-2-（3-甲氧基苯氧基）乙酰肼衍生物（4a-f）/ 1-（4-取代的苯基）-2-[（5-[（3-甲氧基苯氧基）甲基] -1,3， 4-恶二唑-2-基）硫]乙烷-1-酮衍生物（6a-f）/ N-（6-取代的苯并噻唑-2-基）-2-[（5-[（3-甲氧基苯氧基）甲基] -1获得了，3，4-恶二唑-2-基）硫代]乙酰胺衍生物（7a-e），并评价了它们对各种革兰氏阳性，革兰氏阴性细菌和真菌的体外抗菌活性。与抗革兰氏阳性细菌的潜力相比，发现该化合物对革兰氏阴性细菌的抗菌潜力更高。还，筛选化合物对作为健康细胞系的两种选定的人类肿瘤细胞系，A549肺，MCF7乳腺癌细胞系和小鼠胚胎成纤维细胞系，NIH / 3T3的抗增殖活性。在所评估的化合物中，与1,3,3,3T3细胞系相反，具有1
• Preparation of Quinolinium Salts Differing in the Length of the Alkyl Side Chain
  作者：Jan Marek、Vladimir Buchta、Ondrej Soukup、Petr Stodulka、Jiri Cabal、Kallol K. Ghosh、Kamil Musilek、Kamil Kuca

  DOI：10.3390/molecules17066386

  日期：——

  Quaternary quinolinium salts differing in alkyl chain length are members of a widespread group of cationic surfactants. These compounds have numerous applications in various branches of industry and research. In this work, the preparation of quinoline-derived cationic surface active agents differing in the length of the side alkyl chains (from C₈ to C₂₀) is described. An HPLC method was successfully

  烷基链长度不同的季喹啉盐是广泛使用的阳离子表面活性剂组的成员。这些化合物在工业和研究的各个分支中有许多应用。在这项工作中，描述了在侧烷基链（从 C₈ 到 C2₀）长度不同的喹啉衍生的阳离子表面活性剂的制备。成功开发了一种 HPLC 方法，用于区分所制备的长链喹啉衍生物系列的所有成员。总之，已经总结了预期测试或使用的一些可能性。使用微量稀释肉汤方法进行的体外测试表明，C12 链长的物质对革兰氏阳性球菌和念珠菌种类具有良好的活性。