2-[5-iodo-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]acetamide | 209971-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[5-iodo-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]acetamide
• 英文别名: 2-(5-iodo-2-(tosylimino)pyridin-1(2H)-yl)acetamide；2-[5-Iodo-2-(4-methylphenyl)sulfonyliminopyridin-1-yl]acetamide
• CAS: 209971-46-0
• 化学式: C₁₄H₁₄IN₃O₃S
• 分子量: 431.254
• InChiKey: FZNHWGZASDXRRI-UHFFFAOYSA-N

物化性质

• 熔点：
  245 °C
• 沸点：
  555.3±60.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[5-iodo-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]acetamide 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 32.0h， 生成 6-碘-1,5-二氢咪唑并[1,2-a]吡啶-2-胺
  参考文献：
  名称：

  基于片段的新型选择性PI3激酶抑制剂的发现

  摘要：

  我们报告了使用片段筛选和基于片段的药物设计来开发PI3γ激酶片段，使其成为领先者。最初的片段命中是通过高浓度生化筛选发现的，然后进行一轮虚拟筛选以鉴定其他配体有效片段。使用结构指导的片段生长和合并策略将这些化合物开发为有效的和配体有效的先导化合物。这导致了一种具有良好代谢稳定性的有效，选择性和细胞可渗透性的PI3γ激酶抑制剂，可用作临床前工具化合物。

  DOI：

  10.1016/j.bmcl.2011.07.117
• 作为产物：
  描述：

  2-氨基-5-碘吡啶 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-[5-iodo-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]acetamide
  参考文献：
  名称：

  Chemoselective Arylsulfenylation of 2-Aminoimidazol[1,2-a]pyridines by Phenyliodine(III) Bis(trifluoroacetate) (PIFA)

  摘要：

  DOI：

  10.1055/s-1998-2078

文献信息

• Structure guided optimization of a fragment hit to imidazopyridine inhibitors of PI3K
  作者：Sabina Pecchi、Zhi-Jie Ni、Wooseok Han、Aaron Smith、Jiong Lan、Matthew Burger、Hanne Merritt、Marion Wiesmann、John Chan、Susan Kaufman、Mark S. Knapp、Johanna Janssen、Kay Huh、Charles F. Voliva

  DOI：10.1016/j.bmcl.2013.06.010

  日期：2013.8

  PI3 kinases are a family of lipid kinases mediating numerous cell processes such as proliferation, migration and differentiation. The PI3 Kinase pathway is often de-regulated in cancer through PI3K alpha overexpression, gene amplification, mutations and PTEN phosphatase deletion. PI3K inhibitors represent therefore an attractive therapeutic modality for cancer treatment. Herein we describe how the potency of a benzothiazole fragment hit was quickly improved based on structural information and how this early chemotype was further optimized through scaffold hopping. This effort led to the identification of a series of 2-acetamido-5-heteroaryl imidazopyridines showing potent in vitro activity against all class I PI3Ks and attractive pharmacokinetic properties. (C) 2013 Elsevier Ltd. All rights reserved.
• Design and biological evaluation of imidazo[1,2-a]pyridines as novel and potent ASK1 inhibitors
  作者：Yoshito Terao、Hideo Suzuki、Masato Yoshikawa、Hiroaki Yashiro、Shiro Takekawa、Yasushi Fujitani、Kengo Okada、Yoshihisa Inoue、Yoshio Yamamoto、Hideyuki Nakagawa、Shuhei Yao、Tomohiro Kawamoto、Osamu Uchikawa

  DOI：10.1016/j.bmcl.2012.10.084

  日期：2012.12

  Imidazo[1,2-a]pyridine derivatives were designed, synthesized, and evaluated as inhibitors of the apoptosis signal-regulating kinase 1 (ASK1). These were based on a benzothiazole derivative that was discovered from high-throughput screening of our compound library. As a result, we identified potent, selective, and orally bioavailable ASK1 inhibitors for wide range of therapeutic targets. (C) 2012 Elsevier Ltd. All rights reserved.