2-cyano-N-(1,1-dioxo-1H-1λ⁶-benzo[b]thiophen-6-yl)acetamide | 1430330-59-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-cyano-N-(1,1-dioxo-1H-1λ⁶-benzo[b]thiophen-6-yl)acetamide
• 英文别名: 2-Cyano-N-(1,1-dioxo-1H-1lambda6-benzo[b]thiophen-6-yl)acetamide；2-cyano-N-(1,1-dioxo-1-benzothiophen-6-yl)acetamide
• CAS: 1430330-59-8
• 化学式: C₁₁H₈N₂O₃S
• 分子量: 248.262
• InChiKey: YJFOAROKHQGAQC-UHFFFAOYSA-N

物化性质

• 沸点：
  623.8±55.0 °C(Predicted)
• 密度：
  1.538±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyano-N-(1,1-dioxo-1H-1λ⁶-benzo[b]thiophen-6-yl)acetamide 、 邻溴苯甲醛 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以94%的产率得到3-(2-bromophenyl)-2-cyano-N-(1,1-dioxo-1H-1λ⁶-benzo[b]thiophen-6-yl)acrylamide
  参考文献：
  名称：

  [EN] STAT3 INHIBITOR
  [FR] INHIBITEUR DE STAT3

  摘要：

  提供了STAT3抑制剂和治疗炎症或过度增殖疾病（例如癌症）的方法。在某些方面，化合物可用于治疗乳腺癌、头颈癌、肺癌、前列腺癌或胰腺癌。

  公开号：

  WO2014113467A1
• 作为产物：
  描述：

  氰乙酸 、 6-氨基苯并噻吩-1，1-二氧烷 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 以81%的产率得到2-cyano-N-(1,1-dioxo-1H-1λ⁶-benzo[b]thiophen-6-yl)acetamide
  参考文献：
  名称：

  Fragment-based drug design and identification of HJC0123 , a novel orally bioavailable STAT3 inhibitor for cancer therapy

  摘要：

  Fragment-based drug design (FBDD) is a promising approach for the generation of lead molecules with enhanced activity and especially drug-like properties against therapeutic targets. Herein, we report the fragment-based drug design, systematic chemical synthesis and pharmacological evaluation of novel scaffolds as potent anticancer agents by utilizing six privileged fragments from known STAT3 inhibitors. Several new molecules such as compounds 5, 12, and 19 that may act as advanced chemical leads have been identified. The most potent compound 5 (HJC0123) has demonstrated to inhibit STAT3 promoter activity, downregulate phosphorylation of STAT3, increase the expression of cleaved caspase-3, inhibit cell cycle progression and promote apoptosis in breast and pancreatic cancer cells with low micromolar to nanomolar IC50 values. Furthermore, compound 5 significantly suppressed estrogen receptor (ER)negative breast cancer MDA-MB-231 xenograft tumor growth in vivo (p.o.), indicating its great potential as an efficacious and orally bioavailable drug candidate for human cancer therapy. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.023

文献信息

• STAT3 INHIBITOR
  申请人：BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM

  公开号：US20150361031A1

  公开（公告）日：2015-12-17

  Provided are STAT3 inhibitors and methods of treating inflammation or a hyperproliferative disease such as, e.g., cancer. In some aspects, compounds may be used to treat breast cancer, a head/neck cancer, a lung cancer, a prostate cancer, or pancreatic cancer.

  提供了STAT3抑制剂和治疗炎症或过度增殖疾病（例如癌症）的方法。在某些方面，化合物可用于治疗乳腺癌、头颈癌、肺癌、前列腺癌或胰腺癌。
• US9562002B2
  申请人：——

  公开号：US9562002B2

  公开（公告）日：2017-02-07
• US9884863B2
  申请人：——

  公开号：US9884863B2

  公开（公告）日：2018-02-06
• [EN] STAT3 INHIBITOR<br/>[FR] INHIBITEUR DE STAT3
  申请人：UNIV TEXAS

  公开号：WO2014113467A1

  公开（公告）日：2014-07-24

  Provided are STAT3 inhibitors and methods of treating inflammation or a hyperproliferative disease such as, e.g., cancer. In some aspects, compounds may be used to treat breast cancer, a head/neck cancer, a lung cancer, a prostate cancer, or pancreatic cancer.

  提供了STAT3抑制剂和治疗炎症或过度增殖疾病（例如癌症）的方法。在某些方面，化合物可用于治疗乳腺癌、头颈癌、肺癌、前列腺癌或胰腺癌。
• Fragment-based drug design and identification of HJC0123 , a novel orally bioavailable STAT3 inhibitor for cancer therapy
  作者：Haijun Chen、Zhengduo Yang、Chunyong Ding、Lili Chu、Yusong Zhang、Kristin Terry、Huiling Liu、Qiang Shen、Jia Zhou

  DOI：10.1016/j.ejmech.2013.01.023

  日期：2013.4

  Fragment-based drug design (FBDD) is a promising approach for the generation of lead molecules with enhanced activity and especially drug-like properties against therapeutic targets. Herein, we report the fragment-based drug design, systematic chemical synthesis and pharmacological evaluation of novel scaffolds as potent anticancer agents by utilizing six privileged fragments from known STAT3 inhibitors. Several new molecules such as compounds 5, 12, and 19 that may act as advanced chemical leads have been identified. The most potent compound 5 (HJC0123) has demonstrated to inhibit STAT3 promoter activity, downregulate phosphorylation of STAT3, increase the expression of cleaved caspase-3, inhibit cell cycle progression and promote apoptosis in breast and pancreatic cancer cells with low micromolar to nanomolar IC50 values. Furthermore, compound 5 significantly suppressed estrogen receptor (ER)negative breast cancer MDA-MB-231 xenograft tumor growth in vivo (p.o.), indicating its great potential as an efficacious and orally bioavailable drug candidate for human cancer therapy. (C) 2013 Elsevier Masson SAS. All rights reserved.