2-chloro-N-(2-chloro-4-methylpyridin-3-yl)acetamide | 1316197-22-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-chloro-N-(2-chloro-4-methylpyridin-3-yl)acetamide
• CAS: 1316197-22-4
• 化学式: C₈H₈Cl₂N₂O
• 分子量: 219.07
• InChiKey: HBUTZXRRDYCMIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(2-chloro-4-methylpyridin-3-yl)acetamide 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 2-chloro-N-(2-(2-(2-chloro-4-methylpyridin-3-ylamino)-2-oxoethylthio)benzo[d]thiazol-6-yl)acetamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Benzothiazole-2-thiol Derivatives as Potential Anticancer Agents

  摘要：

  研究人员合成了一系列新型苯并噻唑-2-硫醇衍生物，并通过 1H-NMR、13C-NMR 和 HRMS (ESI) 确定了它们的结构。研究了所有化合物对不同类型人类癌细胞株的影响。其中，与苯并噻唑-2-硫醇相连的吡啶基-2-胺化合物 7d、7e、7f 和 7i 具有强效、广谱的抑制活性。化合物 7e 对 SKRB-3（IC50 = 1.2 nM）、SW620（IC50 = 4.3 nM）、A549（IC50 = 44 nM）和 HepG2（IC50 = 48 nM）的抗癌活性最强，并能诱导 HepG2 癌细胞凋亡。

  DOI：

  10.3390/molecules17043933
• 作为产物：
  描述：

  2-氯-3-氨基-4-甲基吡啶 、 氯乙酰氯 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 2-chloro-N-(2-chloro-4-methylpyridin-3-yl)acetamide
  参考文献：
  名称：

  N-(取代苯基)-2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfanyl)乙酰胺作为抗菌剂、抗抑郁剂和抗惊厥剂的合成和生物学评价

  摘要：

  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。

  DOI：

  10.1134/s1068162015020144

文献信息

• Novel small molecules as apoptosis inducers: Synthesis, preliminary structure–activity relationships, and in vitro biological evaluation
  作者：Lifeng Zhao、Xiao Li、Lidan Zhang、Tinghong Ye、Yongxia Zhu、Yuquan Wei、Shengyong Yang、Luoting Yu

  DOI：10.1016/j.bmcl.2013.02.076

  日期：2013.4

  Inducing apoptosis is a promising therapeutic approach to overcome cancer. In this study, 30 compounds were synthesized and evaluated for their antiproliferative activity against three tumor cell lines in vitro: A875, H460 and Hela cancer cells by the MTT assay. The most potent analogue 7a, a novel compound was first reported by our group, inhibited the proliferation of A875 cells with an IC50 value of 98 nM. Flow cytometry analysis and morphological analysis suggested that compound 7a had potential anticancer efficacy via G(2)/M cell cycle arrest, which could be attributed to its proliferation and apoptosis, and also in a concentration-dependent manner. The SAR analysis indicated that the substituents R-2 played a crucial role in the antiproliferation activity. (C) 2013 Elsevier Ltd. All rights reserved.
• 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。
• Synthesis and Biological Evaluation of Novel Benzothiazole-2-thiol Derivatives as Potential Anticancer Agents
  作者：Xuan-Hong Shi、Zhao Wang、Yong Xia、Ting-Hong Ye、Mei Deng、You-Zhi Xu、Yu-Quan Wei、Luo-Ting Yu

  DOI：10.3390/molecules17043933

  日期：——

  A series of novel benzothiazole-2-thiol derivatives were synthesized and their structures determined by 1H-NMR, 13C-NMR and HRMS (ESI). The effects of all compounds on a panel of different types of human cancer cell lines were investigated. Among them, pyridinyl-2-amine linked benzothiazole-2-thiol compounds 7d, 7e, 7f and 7i exhibited potent and broad-spectrum inhibitory activities. Compound 7e displayed the most potent anticancer activity on SKRB-3 (IC50 = 1.2 nM), SW620 (IC50 = 4.3 nM), A549 (IC50 = 44 nM) and HepG2 (IC50 = 48 nM) and was found to induce apoptosis in HepG2 cancer cells.

  研究人员合成了一系列新型苯并噻唑-2-硫醇衍生物，并通过 1H-NMR、13C-NMR 和 HRMS (ESI) 确定了它们的结构。研究了所有化合物对不同类型人类癌细胞株的影响。其中，与苯并噻唑-2-硫醇相连的吡啶基-2-胺化合物 7d、7e、7f 和 7i 具有强效、广谱的抑制活性。化合物 7e 对 SKRB-3（IC50 = 1.2 nM）、SW620（IC50 = 4.3 nM）、A549（IC50 = 44 nM）和 HepG2（IC50 = 48 nM）的抗癌活性最强，并能诱导 HepG2 癌细胞凋亡。