5,6-Dimethoxy-2-(4-nitro-phenyl)-benzothiazole | 162374-70-1

• 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: 5,6-Dimethoxy-2-(4-nitro-phenyl)-benzothiazole
• 英文别名: 5,6-Dimethoxy-2-(4-nitrophenyl)-1,3-benzothiazole
• CAS: 162374-70-1
• 化学式: C₁₅H₁₂N₂O₄S
• 分子量: 316.337
• InChiKey: VUHSTFXSDBXHSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6-Dimethoxy-2-(4-nitro-phenyl)-benzothiazole 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以89%的产率得到4-(5,6-dimethoxy-benzothiazol-2-yl)-aniline
  参考文献：
  名称：

  Antitumor Benzothiazoles. 3. Synthesis of 2-(4-Aminophenyl)benzothiazoles and Evaluation of Their Activities against Breast Cancer Cell Lines in Vitro and in Vivo

  摘要：

  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.

  DOI：

  10.1021/jm9600959
• 作为产物：
  描述：

  N-(3,4-dimethoxyphenyl)-4-nitrobenzamide 在 劳森试剂 、 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 六甲基磷酰三胺 、 乙醇 为溶剂， 反应 6.5h， 生成 5,6-Dimethoxy-2-(4-nitro-phenyl)-benzothiazole
  参考文献：
  名称：

  Antitumor Benzothiazoles. 3. Synthesis of 2-(4-Aminophenyl)benzothiazoles and Evaluation of Their Activities against Breast Cancer Cell Lines in Vitro and in Vivo

  摘要：

  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.

  DOI：

  10.1021/jm9600959

文献信息

• 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.