5-氯甲基噻唑-2-羧酸乙酯 | 175675-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氯甲基噻唑-2-羧酸乙酯
• 英文名称: 5-chloromethylthiazole-2-carboxylic acid ethyl ester
• 英文别名: ethyl 5-(chloromethyl)-1,3-thiazole-2-carboxylate
• CAS: 175675-74-8
• 化学式: C₇H₈ClNO₂S
• 分子量: 205.665
• InChiKey: MCTAWJVLEBVJTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-5-苯并噻唑 、 5-氯甲基噻唑-2-羧酸乙酯 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Searching for New Cures for Tuberculosis: Design, Synthesis, and Biological Evaluation of 2-Methylbenzothiazoles

  摘要：

  The actual development and clinical use of new therapeutics for tuberculosis (TB) have remained stagnant for years because of the complexity of the disease process, the treatment of which at present requires the administration of drug combinations over a 6 month period. There is thus all urgent need for the discovery and development of novel, more active, and less toxic anti-TB agents. In this study, we report on the chemistry and biology of a series of potent 5-(2-methylbenzothiazol-5-yloxy-methyl)isoxazole-3-carboxamide derivatives, which proved to be active against replicating Mycobacterium tuberculosis (Mtb) H(37)Rv. The most potent compounds 7j and 7s were found to inhibit Mtb growth at micromolar concentrations, with MIC values of 1.4 and 1.9 mu M, respectively. Impressively, all active compounds were nontoxic toward Vero cells (IC50 > 128 mu M). Moreover, the best of these compounds were also tested against protozoan parasites, and some of these compounds were found to show activity, especially against Plasmodium falciparum. These studies thus suggest that certain 2-methylbenzothiazole based compounds may serve as promising lead scaffolds for further elaboration as anti-TB drugs and as possible antimalaria drugs.

  DOI：

  10.1021/jm901112f
• 作为产物：
  描述：

  硫代草氨酸乙酯 、 1,3-二氯丙酮 以 甲苯 为溶剂， 反应 2.0h， 生成 5-氯甲基噻唑-2-羧酸乙酯
  参考文献：
  名称：

  Searching for New Cures for Tuberculosis: Design, Synthesis, and Biological Evaluation of 2-Methylbenzothiazoles

  摘要：

  The actual development and clinical use of new therapeutics for tuberculosis (TB) have remained stagnant for years because of the complexity of the disease process, the treatment of which at present requires the administration of drug combinations over a 6 month period. There is thus all urgent need for the discovery and development of novel, more active, and less toxic anti-TB agents. In this study, we report on the chemistry and biology of a series of potent 5-(2-methylbenzothiazol-5-yloxy-methyl)isoxazole-3-carboxamide derivatives, which proved to be active against replicating Mycobacterium tuberculosis (Mtb) H(37)Rv. The most potent compounds 7j and 7s were found to inhibit Mtb growth at micromolar concentrations, with MIC values of 1.4 and 1.9 mu M, respectively. Impressively, all active compounds were nontoxic toward Vero cells (IC50 > 128 mu M). Moreover, the best of these compounds were also tested against protozoan parasites, and some of these compounds were found to show activity, especially against Plasmodium falciparum. These studies thus suggest that certain 2-methylbenzothiazole based compounds may serve as promising lead scaffolds for further elaboration as anti-TB drugs and as possible antimalaria drugs.

  DOI：

  10.1021/jm901112f

文献信息

• METHOD FOR CONTROLLING ARTHROPOD PEST
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20150344466A1

  公开（公告）日：2015-12-03

  An amide compound represented by formula (I): [wherein A represents a 3- to 7-membered saturated heterocyclic ring which contains, as ring-forming component(s), one or more atoms or groups selected from the group consisting of an oxygen atom and —S(O) t —, t represents 0, etc., R 1 and R 2 are the same or different and represent a hydrogen atom, etc., n represents 0, etc., the following formula (II): represents a 5-membered aromatic ring, in which Z represents a nitrogen atom or a carbon atom and X 1 , X 2 and X 3 are the same or different and represent a nitrogen atom, etc., R 3 and R 4 are the same or different and represent a hydrogen atom, etc., m represents 0 to 2, Q represents one group selected from group A or a C1 to C8 chain hydrocarbon group optionally having one group selected from group A, Y represents an oxygen atom, etc., u represents 0, etc., and v represents 0, etc.] has excellent arthropod pest controlling effects.

  化合物式(I)所代表的酰胺化合物：[其中A代表一个3到7个成员的饱和杂环环，该环包含作为环构成组分之一或多个原子或基团，所选自氧原子和—S（O）t—群，t代表0等；R1和R2相同或不同，代表氢原子等；n代表0等；下列式子(II)代表一个5个成员的芳香环，在该环中Z代表一个氮原子或一个碳原子，X1、X2和X3相同或不同，代表氮原子等，R3和R4相同或不同，代表氢原子等，m代表0到2，Q代表从群A中选择的一个群或一个C1到C8链烃基团，该基团可以选择从群A中选择的一个群，Y代表氧原子等，u代表0等，v代表0等]具有优良的节肢动物害虫控制效果。
• Amide compound, an arthropod pest control agent and a method for controlling arthropod pest
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2952096B1

  公开（公告）日：2018-04-04
• US9814235B2
  申请人：——

  公开号：US9814235B2

  公开（公告）日：2017-11-14
• [EN] SPIRO COMPOUND AND DRUG FOR ACTIVATING ADIPONECTIN RECEPTOR<br/>[FR] COMPOSÉ SPIRO ET MÉDICAMENT POUR ACTIVER LE RÉCEPTEUR D'ADIPONECTINE
  申请人：NISSAN CHEMICAL IND LTD

  公开号：WO2011142359A1

  公开（公告）日：2011-11-17

  　アディポネクチン受容体親和性及びアゴニスト作用を有し、メタボリックシンドローム、特に肥満や糖尿病を伴うメタボリックシンドローム、および動脈硬化などの予防又は治療に有用な新規な医薬を提供することを課題とする。　式（Ｉ）（式中のＺ１、Ｘ、Ｌ１、Ｌ２、Ｅ、Ｒ６、Ｒ７、ｍ、ｎ、Ｔは、本文中において定義される。）で表される新規スピロ化合物、該化合物の互変異性体、若しくはその医薬的に許容され得る塩を提供するものである。
• Searching for New Cures for Tuberculosis: Design, Synthesis, and Biological Evaluation of 2-Methylbenzothiazoles
  作者：Qingqing Huang、Jialin Mao、Baojie Wan、Yuehong Wang、Reto Brun、Scott G. Franzblau、Alan P. Kozikowski

  DOI：10.1021/jm901112f

  日期：2009.11.12

  The actual development and clinical use of new therapeutics for tuberculosis (TB) have remained stagnant for years because of the complexity of the disease process, the treatment of which at present requires the administration of drug combinations over a 6 month period. There is thus all urgent need for the discovery and development of novel, more active, and less toxic anti-TB agents. In this study, we report on the chemistry and biology of a series of potent 5-(2-methylbenzothiazol-5-yloxy-methyl)isoxazole-3-carboxamide derivatives, which proved to be active against replicating Mycobacterium tuberculosis (Mtb) H(37)Rv. The most potent compounds 7j and 7s were found to inhibit Mtb growth at micromolar concentrations, with MIC values of 1.4 and 1.9 mu M, respectively. Impressively, all active compounds were nontoxic toward Vero cells (IC50 > 128 mu M). Moreover, the best of these compounds were also tested against protozoan parasites, and some of these compounds were found to show activity, especially against Plasmodium falciparum. These studies thus suggest that certain 2-methylbenzothiazole based compounds may serve as promising lead scaffolds for further elaboration as anti-TB drugs and as possible antimalaria drugs.