2-(2-Chloro-4-nitrophenyl)benzothiazole | 174536-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(2-Chloro-4-nitrophenyl)benzothiazole
• 英文别名: 2-(2-Chloro-4-nitrophenyl)-1,3-benzothiazole
• CAS: 174536-60-8
• 化学式: C₁₃H₇ClN₂O₂S
• 分子量: 290.73
• InChiKey: CGEZGBMNRWUEPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-Chloro-4-nitrophenyl)benzothiazole 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以93%的产率得到4-苯并噻唑-2-基-3-氯苯胺
  参考文献：
  名称：

  Stevens, Malcolm F. G.; Shi, Dong-Fang; Castro, Angeles, Journal of the Chemical Society. Perkin transactions I, 1996, # 1, p. 83 - 94

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-4-硝基苯甲酰氯 、 2-氨基苯硫醇 在 吡啶 作用下， 反应 1.0h， 以74%的产率得到2-(2-Chloro-4-nitrophenyl)benzothiazole
  参考文献：
  名称：

  Stevens, Malcolm F. G.; Shi, Dong-Fang; Castro, Angeles, Journal of the Chemical Society. Perkin transactions I, 1996, # 1, p. 83 - 94

  摘要：

  DOI：

文献信息

• Design, Synthesis, Biological Evaluation and In Silico Studies of Few Novel 2-Substituted Benzothiazole Derivatives as Potential EGFR Inhibitors
  作者：Muhammad Mubeen、Suvarna Ganesh Kini、Avinash Kumar、Karkala Sreedhara Ranganath Pai

  DOI：10.2174/1570180816666181108112228

  日期：2019.8.8

  suggests that benzothiazole derivatives have good potential to exhibit anticancer activity. Compounds that inhibit the kinase activity of EGFR are of potential interest as new antitumor agent. Objective: To design, synthesize and carry out in silico along with biological evaluation of 2- substituted benzothiazole compounds with EGFR inhibitory activity. Methods: Benzothiazole derivatives designed from

  背景：对新的抗癌小分子疗法存在巨大的未满足的医疗需求。详尽的文献综述表明，苯并噻唑衍生物具有良好的抗癌活性潜力。抑制 EGFR 激酶活性的化合物作为新的抗肿瘤剂具有潜在的意义。目的：设计、合成具有EGFR抑制活性的2-取代苯并噻唑化合物并在计算机上进行生物学评价。方法：基于分子对接方法设计的苯并噻唑衍生物用于潜在的EGFR酪氨酸激酶抑制，基于对接结果合成并表征。进行了 Insilico 研究以了解我们的分子抑制 EGFR 酶的模式。作为初步研究，首先筛选这些化合物的抗氧化活性，然后筛选针对 MCF-7 细胞系和 A549 细胞系的抗癌活性。结果：与标准药物阿霉素相比，化合物B5对MCF-7细胞系显示出有效的抗癌活性，IC50值为9.7μM，化合物B8对A549细胞系显示出显着的抗癌活性，IC50值为49.7μM（IC50 = 1.4μM） A549 细胞系上的 MCF-7 和 1.0μM）。在
• Antitumor Benzothiazoles. 3. Synthesis of 2-(4-Aminophenyl)benzothiazoles and Evaluation of Their Activities against Breast Cancer Cell Lines <i>in </i><i>Vitro </i>and <i>in Vivo</i>
  作者：Dong-Fang Shi、Tracey D. Bradshaw、Samantha Wrigley、Carol J. McCall、Peter Lelieveld、Iduna Fichtner、Malcolm F. G. Stevens

  DOI：10.1021/jm9600959

  日期：1996.1.1

  A new series of 2-(4-aminophenyl)benzothiazoles substituted in the phenyl ring and benzothiazole moiety has been synthesized by simple, high-yielding routes. The parent molecule 5a shows potent inhibitory activity in vitro in the nanomolar range against a panel of human breast cancer cell lines, but is inactive (IC50 > 30 mu M) against other cell types: activity against the sensitive breast lines MCF-7 and MDA 468 is characterized by a biphasic dose-response relationship. Structure-activity relationships derived using these cell types has revealed that activity follows the heterocyclic sequence benzothiazole > benzoxazole much greater than benzimidazole and that 2-(4-aminophenyl)benzothiazoles bearing a 3'-methyl- 9a, 3'-bromo- 9c, 3'- iodo- 9f, and 3'-chloro-substituent 9i are especially potent and their activity extends to ovarian, lung, and renal cell lines. Four compounds have been evaluated in vivo against human mammary carcinoma models in nude mice. Compound 9a showed the most potent growth inhibition against the ER(+) (MCF-7 and BO) and ER(-) (MT-1 and MT-3) tumors. Our efforts to identify a pharmacological mechanism of action for these intriguing compounds have not, as yet, been successful.
• Solid phase combinatorial synthesis of benzothiazoles and evaluation of topoisomerase II inhibitory activity
  作者：Suk-June Choi、Hyen Joo Park、Sang Kook Lee、Sang Woong Kim、Gyoonhee Han、Hea-Young Park Choo

  DOI：10.1016/j.bmc.2005.09.051

  日期：2006.2

  To investigate one possible mechanism of action of the cytotoxic activity of benzothiazoles, we synthesized 2-(substituted-phenyl)benzothiazoles and evaluated their ability to inhibit topoisomerase 11 activities. Solid phase combinatorial method using trityl resin was employed and benzothiazole derivatives with Various substitution on 2'-, 3'-, or 4'-position of phenyl group were obtained in ca. 30 mg scale (7-96% yield). Most of the compounds synthesized exhibited topoisomerase 11 inhibitory activity at 100 mu M. 2-(3-Amino-4-methylphenyl)benzothiazole showed high activity (IC50 = 71.7 mu M), comparable to etoposide (IC50 = 78.4 mu M). (c) 2005 Elsevier Ltd. All rights reserved.
• BENZAZOLE COMPOUNDS FOR USE IN THERAPY
  申请人：CANCER RESEARCH CAMPAIGN TECHNOLOGY LIMITED

  公开号：EP0721336A1

  公开（公告）日：1996-07-17
• Methods and compositions for the treatment of neurodegenerative disorders
  申请人：Jin Xiaowei

  公开号：US20080044390A1

  公开（公告）日：2008-02-21

  The present invention features compositions, kits, and methods for treating, preventing, and ameliorating neurodegenerative disorders, e.g., Huntington's disease.