2-bromo-4'-(methylthio)acetanilide | 150221-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-4'-(methylthio)acetanilide
• 英文别名: 2-bromo-N-(4-methylsulfanylphenyl)acetamide
• CAS: 150221-08-2
• 化学式: C₉H₁₀BrNOS
• 分子量: 260.154
• InChiKey: MRIOJWPNRGTVQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-4'-(methylthio)acetanilide 、 噻菌灵 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 N-(4-methylsulfanylphenyl)-2-(2-thiazol-4-ylbenzimidazol-1-yl)acetamide
  参考文献：
  名称：

  Structure–activity relationship study of selective benzimidazole-based inhibitors of Cryptosporidium parvum IMPDH

  摘要：

  Cryptosporidium parasites are important waterborne pathogens of both humans and animals. The Cryptosporidium parvum and Cryptosporidium hominis genomes indicate that the only route to guanine nucleotides is via inosine 5 '-monophosphate dehydrogenase (IMPDH). Thus the inhibition of the parasite IMPDH presents a potential strategy for treating Cryptosporidium infections. A selective benzimidazole-based inhibitor of C. parvum IMPDH (CpIMPDH) was previously identified in a high throughput screen. Here we report a structure-activity relationship study of benzimidazole-based compounds that resulted in potent and selective inhibitors of CpIMPDH. Several compounds display potent antiparasitic activity in vitro. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.029
• 作为产物：
  描述：

  溴乙酰溴 、 4-氨基茴香硫醚 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-bromo-4'-(methylthio)acetanilide
  参考文献：
  名称：

  (Quinazoline 4-yloxy)acetamide 和 (4-oxoquinazoline-3(4H)-yl)acetamide 衍生物作为结核分枝杆菌 bd 氧化酶抑制剂的设计、合成和生物学评价

  摘要：

  治疗耐药结核病迫切需要具有新作用机制的新型化学支架。结核分枝杆菌的氧化磷酸化途径由多个临床验证的药物靶点组成。该途径可以通过两种末端氧化酶中的任何一种发挥作用——质子泵细胞色素bc 1 -aa 3超复合物，或能量效率较低但亲和力高的细胞色素bd氧化酶。已发现单独抑制bc 1复合物是抑菌的而不是杀菌的。另一方面，对这两种氧化酶的抑制对病原体都是致命的。在本研究中，我们使用了bc 1结核分枝杆菌的复杂突变体筛选 (Quinazoline 4-yloxy) 乙酰胺和 (4-oxoquinazoline-3(4 H )-yl) 乙酰胺衍生物对抗交替氧化酶，即细胞色素bd氧化酶。发现两种分子 S-021-0601 和 S-021-0607 抑制突变体的 MIC 分别为 8 和 16 μM，而对野生型结核分枝杆菌的 MIC 分别为 128 和 256 μM 。在野生型中，其中一种化合物与bc 1抑制剂

  DOI：

  10.1016/j.ejmech.2022.114639

文献信息

• Pyridazine derivatives and drugs containing the same as the active ingredient
  申请人：Kowa Co., Ltd.

  公开号：US06403586B1

  公开（公告）日：2002-06-11

  This invention relates to pyridazine derivatives represented by the formula (1): wherein R1 represents a lower alkoxyl group, a lower alkylthio group or a halogen atom; R2 represents H, a lower alkoxyl group, a lower alkylthio group or a halogen atom; R3 represents a lower alkyl or lower alkenyl group, which may be substituted by one or more OHs, CNs, lower cycloalkyl groups, (substituted) aromatic groups or (substituted) carbamoyl groups; R4 represents COOH, a lower alkoxycarbonyl group, a (substituted) carbamoyl group, a (substituted) amino group, or a (substituted) ureido group; and the dashed line indicates that the carbon-carbon bond between the 4-position and the 5-position is a single bond or a double bond, or salts thereof; and also to medicines containing them as effective ingredients. These compounds have excellent inhibitory activity against interleukin-1&bgr; production, and are useful as preventives and therapeutics for immune system diseases, inflammatory diseases, ischemic diseases and the like.

  这项发明涉及由式（1）表示的吡啶嗪衍生物： 其中R1代表较低的烷氧基团、较低的烷硫基团或卤原子；R2代表H、较低的烷氧基团、较低的烷硫基团或卤原子；R3代表较低的烷基或较低的烯基，可以被一个或多个OH、CN、较低的环烷基、（取代的）芳香基或（取代的）氨基甲酰基取代；R4代表COOH、较低的烷氧羰基团、（取代的）氨基甲酰基、（取代的）氨基团或（取代的）脲基；虚线表示4位和5位之间的碳-碳键是单键或双键，或其盐；以及含有它们作为有效成分的药物。这些化合物对白细胞介素-1β的产生具有出色的抑制活性，并可用作免疫系统疾病、炎症性疾病、缺血性疾病等的预防和治疗药物。
• NOVEL PYRIDAZINE DERIVATIVES AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：Kowa Co., Ltd.

  公开号：EP1061077A1

  公开（公告）日：2000-12-20

  This invention relates to pyridazine derivatives represented by the formula (1): wherein R1 represents a lower alkoxyl group, a lower alkylthio group or a halogen atom; R2 represents H, a lower alkoxyl group, a lower alkylthio group or a halogen atom; R3 represents a lower alkyl or lower alkenyl group, which may be substituted by one or more OHs, CNs, lower cycloalkyl groups, (substituted) aromatic groups or (substituted) carbamoyl groups; R4 represents COOH, a lower alkoxycarbonyl group, a (substituted) carbamoyl group, a (substituted) amino group, or a (substituted) ureido group; and the dashed line indicates that the carbon-carbon bond between the 4-position and the 5-position is a single bond or a double bond, or salts thereof; and also to medicines containing them as effective ingredients. These compounds have excellent inhibitory activity against interleukin-1β production, and are useful as preventives and therapeutics for immune system diseases, inflammatory diseases, ischemic diseases and the like.

  本发明涉及式（1）所代表的哒嗪衍生物： 其中 R1 代表低级烷氧基、低级烷硫基或卤原子；R2 代表 H、低级烷氧基、低级烷硫基或卤原子；R3 代表低级烷基或低级烯基，可被一个或多个 OH、CN、低级环烷基、（取代的）芳香基团或（取代的）氨基甲酰基取代；R4 代表 COOH、低级烷氧羰基、（取代的）氨基甲酰基、（取代的）氨基或 （取代的）脲基；虚线表示 4 位和 5 位之间的碳-碳键为单键或双键，或其盐类；以及含有它们作为有效成分的药物。这些化合物对白细胞介素-1β的产生具有良好的抑制活性，可作为免疫系统疾病、炎症性疾病、缺血性疾病等的预防和治疗药物。
• US6403586B1
  申请人：——

  公开号：US6403586B1

  公开（公告）日：2002-06-11
• Structure–activity relationship study of selective benzimidazole-based inhibitors of Cryptosporidium parvum IMPDH
  作者：Sivapriya Kirubakaran、Suresh Kumar Gorla、Lisa Sharling、Minjia Zhang、Xiaoping Liu、Soumya S. Ray、Iain S. MacPherson、Boris Striepen、Lizbeth Hedstrom、Gregory D. Cuny

  DOI：10.1016/j.bmcl.2012.01.029

  日期：2012.3

  Cryptosporidium parasites are important waterborne pathogens of both humans and animals. The Cryptosporidium parvum and Cryptosporidium hominis genomes indicate that the only route to guanine nucleotides is via inosine 5 '-monophosphate dehydrogenase (IMPDH). Thus the inhibition of the parasite IMPDH presents a potential strategy for treating Cryptosporidium infections. A selective benzimidazole-based inhibitor of C. parvum IMPDH (CpIMPDH) was previously identified in a high throughput screen. Here we report a structure-activity relationship study of benzimidazole-based compounds that resulted in potent and selective inhibitors of CpIMPDH. Several compounds display potent antiparasitic activity in vitro. (C) 2012 Elsevier Ltd. All rights reserved.
• Design, synthesis and biological evaluation of (Quinazoline 4-yloxy)acetamide and (4-oxoquinazoline-3(4H)-yl)acetamide derivatives as inhibitors of Mycobacterium tuberculosis bd oxidase
  作者：Amit Kumar、Neetu Kumari、Sandeep Bhattacherjee、Umamageswaran Venugopal、Shahid Parwez、Mohammad Imran Siddiqi、Manju Y. Krishnan、Gautam Panda

  DOI：10.1016/j.ejmech.2022.114639

  日期：2022.11

  affinity cytochrome bd oxidase. Inhibiting the bc1 complex alone has been found bacteriostatic and not bactericidal. On the other hand, inhibition of both these oxidases turns lethal to the pathogen. In the present study, we used a bc1 complex mutant of M. tuberculosis to screen (Quinazoline 4-yloxy)acetamide and (4-oxoquinazoline-3(4H)-yl)acetamide derivatives against the alternate oxidase, i.e., cytochrome

  治疗耐药结核病迫切需要具有新作用机制的新型化学支架。结核分枝杆菌的氧化磷酸化途径由多个临床验证的药物靶点组成。该途径可以通过两种末端氧化酶中的任何一种发挥作用——质子泵细胞色素bc 1 -aa 3超复合物，或能量效率较低但亲和力高的细胞色素bd氧化酶。已发现单独抑制bc 1复合物是抑菌的而不是杀菌的。另一方面，对这两种氧化酶的抑制对病原体都是致命的。在本研究中，我们使用了bc 1结核分枝杆菌的复杂突变体筛选 (Quinazoline 4-yloxy) 乙酰胺和 (4-oxoquinazoline-3(4 H )-yl) 乙酰胺衍生物对抗交替氧化酶，即细胞色素bd氧化酶。发现两种分子 S-021-0601 和 S-021-0607 抑制突变体的 MIC 分别为 8 和 16 μM，而对野生型结核分枝杆菌的 MIC 分别为 128 和 256 μM 。在野生型中，其中一种化合物与bc 1抑制剂