7-甲氧基-2-甲基-1,3-苯并噻唑 | 163298-70-2

• 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: 7-甲氧基-2-甲基-1,3-苯并噻唑
• 英文名称: 7-methoxy-2-methylbenzo[d]thiazole
• 英文别名: 7-Methoxy-2-methyl-benzothiazol；7-methoxy-2-methyl-benzothiazole；7-methoxy-2-methyl-1,3-benzothiazole
• CAS: 163298-70-2
• 化学式: C₉H₉NOS
• mdl: MFCD07423416
• 分子量: 179.243
• InChiKey: ULNOESYCOCNVQV-UHFFFAOYSA-N

物化性质

• 熔点：
  56-57 °C(Solv: ligroine (8032-32-4))
• 沸点：
  284.2±13.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-甲氧基-2-甲基-1,3-苯并噻唑 在 三氯化铝 、 sodium ethanolate 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 2.5h， 生成 2-Oxalomethyl-6-oxopyrano<3,2-g>-benzothiazol-8-carbonsaeure
  参考文献：
  名称：

  药理活性的4-氧代-4 H-铬-2-羧酸（2-羧基色酮）。第一部分。稠合噻唑环的4-氧代-4 H-铬-2--2-羧酸的合成

  摘要：

  描述了五个含有稠合的2-甲基噻唑环的2-羧基色酮的合成。所有这些均得自适当取代的乙酰基羟基苯并噻唑，它们是通过几种途径合成的，但主要是通过在各种条件下将甲氧基苯并噻唑进行乙酰化而合成的。包括有关2-甲基噻唑并色酮酸的质谱裂解的注释。

  DOI：

  10.1039/j39700001553
• 作为产物：
  描述：

  3’-甲氧基乙酰苯胺 在 劳森试剂 、 potassium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 氯苯 为溶剂， 反应 3.5h， 生成 7-甲氧基-2-甲基-1,3-苯并噻唑
  参考文献：
  名称：

  [EN] ANTI-CANCER COMPOUNDS
  [FR] COMPOSÉS ANTI-CANCEREUX

  摘要：

  提供了治疗癌症等疾病的方法和组合物。在某些方面，提供了可以抑制Skp2的化合物。具体地，披碱酮衍生物被揭示具有减少多能、多潜能或全能细胞分化的能力，因此在治疗癌症等增生性疾病中具有治疗效用。

  公开号：

  WO2015010032A1

文献信息

• Compounds enhancing antitumor activity of other cytotoxic agents
  申请人：Pfizer Inc

  公开号：US06130217A1

  公开（公告）日：2000-10-10

  This invention relates to certain heterocyclic compounds and their pharmaceutically acceptable salts, which are useful for sensitizing multidrug-resistant tumor cells to anticancer agents and multidrug resistant forms of malaria, tuberculosis, leishmania and amoebic dysentery to chemotherapeutants. The compounds and their pharmaceutically acceptable salts are also inhibitors of the active drug transport capability of P-glycoprotein which is encoded by the human MDR1 gene, as well as of certain other related ATP-binding-cassette transporters from eukaryotic and prokaryotic organisms (e.g., pfmdr from Plasmodium falciprum, and murine mdr1 and mdr3 gene products).

  本发明涉及某些杂环化合物及其药学上可接受的盐，这些化合物可用于增强多药耐药肿瘤细胞对抗癌药物的敏感性，以及对抗多药耐药的疟疾、结核病、利什曼病和阿米巴痢疾的化疗药物。这些化合物及其药学上可接受的盐还是P-糖蛋白的活性药物转运能力的抑制剂，该蛋白由人类MDR1基因编码，以及来自真核生物和原核生物的某些其他相关ATP结合盒转运体（例如来自疟原虫恶性疟原虫的pfmdr，以及小鼠mdr1和mdr3基因产物）。
• 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.
• Kiprianow; Daschewskaja, Zhurnal Obshchei Khimii, 1949, vol. 19, p. 1158,1159, 1164; engl. Ausg. S. 1153, 1154,1159
  作者：Kiprianow、Daschewskaja

  DOI：——

  日期：——
• Mizuno et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1956, vol. 76, p. 329,332
  作者：Mizuno et al.

  DOI：——

  日期：——
• Sweschnikow; Lewkoew, Zhurnal Obshchei Khimii, 1946, vol. 16, p. 1071,1072, 1073
  作者：Sweschnikow、Lewkoew

  DOI：——

  日期：——