N-(benzo[d][1,3]dioxol-5-yl)benzo[b]thiophene-3-carboxamide | 915935-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N-(benzo[d][1,3]dioxol-5-yl)benzo[b]thiophene-3-carboxamide
• 英文别名: N-(1,3-benzodioxol-5-yl)-1-benzothiophene-3-carboxamide
• CAS: 915935-10-3
• 化学式: C₁₆H₁₁NO₃S
• mdl: MFCD08724317
• 分子量: 297.334
• InChiKey: GPWAXQZJIXCIPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  75.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(benzo[d][1,3]dioxol-5-yl)benzo[b]thiophene-3-carboxamide 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以34 %的产率得到N-(benzo[d][1,3]dioxol-5-yl)benzo[b]thiophene-3-carboxamide 1,1-dioxide
  参考文献：
  名称：

  苯并[b]噻吩-3-羧酸 1,1-二氧化衍生物作为靶向 RhoA/ROCK 通路的抗癌剂的合成和体外评价

  摘要：

  Rho 家族 GTP 酶调节细胞过程并促进肿瘤生长和转移;因此，RhoA 是肿瘤转移抑制的潜在靶点。然而，目前的进展有限。

  DOI：

  10.1080/14756366.2024.2390911
• 作为产物：
  描述：

  N-(6-acetyl-1,3-benzodioxol-5-yl)-1-benzothiophene-3-carboxamide 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以28%的产率得到N-(benzo[d][1,3]dioxol-5-yl)benzo[b]thiophene-3-carboxamide
  参考文献：
  名称：

  Design and Synthesis of 2-(3-Benzo[b]thienyl)-6,7-methylenedioxyquinolin-4-one Analogues as Potent Antitumor Agents that Inhibit Tubulin Assembly

  摘要：

  As part of our continuing investigation of azo-flavonoid derivatives as potential anticancer drug candidates, a series of 2-aryl-6,7-methylenedioxyquinolin-4-one analogues was designed and synthesized. The design combined structural features of 2-(2-fluorophenyl)-6,7-methylenedioxyquinolin-4-one (CHM-1), a previously discovered compound with potent in vivo antitumor activity, and 2-arylquinolin-4-ones, identified by CoMFA models, The newly synthesized analogues were evaluated for cytotoxicity against seven human cancer cell lines, and structure-activity relationship (SAR) correlations were established. Analogues 1, 37, and 39 showed potent cytotoxicity against different cancer cell lines. Compound I demonstrated selective cytotoxicity against Hep 3B (hepatoma) cells. Compound 37 was cytotoxic against HL-60 (leukemia), HCT-116 (colon cancer), Hep 3B (hepatoma), and SK-MEL-5 (melanoma) cells. Compound 39 exhibited broad cytotoxicity against all seven cancer cell lines, with IC50 values between 0.07and 0.19 mu M. Results from mechanism of action studies revealed that these new quinolone derivatives function as antitubulin agents.

  DOI：

  10.1021/jm900456w

文献信息

• Design and Synthesis of 2-(3-Benzo[<i>b</i>]thienyl)-6,7-methylenedioxyquinolin-4-one Analogues as Potent Antitumor Agents that Inhibit Tubulin Assembly
  作者：Yu-Hsun Chang、Mei-Hua Hsu、Sheng-Hung Wang、Li-Jiau Huang、Keduo Qian、Susan L. Morris-Natschke、Ernest Hamel、Sheng-Chu Kuo、Kuo-Hsiung Lee

  DOI：10.1021/jm900456w

  日期：2009.8.13

  As part of our continuing investigation of azo-flavonoid derivatives as potential anticancer drug candidates, a series of 2-aryl-6,7-methylenedioxyquinolin-4-one analogues was designed and synthesized. The design combined structural features of 2-(2-fluorophenyl)-6,7-methylenedioxyquinolin-4-one (CHM-1), a previously discovered compound with potent in vivo antitumor activity, and 2-arylquinolin-4-ones, identified by CoMFA models, The newly synthesized analogues were evaluated for cytotoxicity against seven human cancer cell lines, and structure-activity relationship (SAR) correlations were established. Analogues 1, 37, and 39 showed potent cytotoxicity against different cancer cell lines. Compound I demonstrated selective cytotoxicity against Hep 3B (hepatoma) cells. Compound 37 was cytotoxic against HL-60 (leukemia), HCT-116 (colon cancer), Hep 3B (hepatoma), and SK-MEL-5 (melanoma) cells. Compound 39 exhibited broad cytotoxicity against all seven cancer cell lines, with IC50 values between 0.07and 0.19 mu M. Results from mechanism of action studies revealed that these new quinolone derivatives function as antitubulin agents.