4-溴-2-氯苯肼 | 206559-39-9

• 物质功能分类: 有机原料 - 肼或胲的有机衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-溴-2-氯苯肼
• 英文名称: 4-bromo-2-chlorobenzohydrazide
• CAS: 206559-39-9
• 化学式: C₇H₆BrClN₂O
• mdl: MFCD00270095
• 分子量: 249.494
• InChiKey: ITRFHDNPGFOLFX-UHFFFAOYSA-N

物化性质

• 熔点：
  173 °C
• 密度：
  1.719±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  4-溴-2-氯苯肼 在 正丁基锂 、 三氟甲磺酸三甲基硅酯 、 silver trifluoromethanesulfonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 3-chloro-4-(5-(1-(4-chlorophenyl)cyclobutyl)-4-methyl-4H-1,2,4-triazol-3-yl)benzamide
  参考文献：
  名称：

  Substituted phenyl triazoles as selective inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1

  摘要：

  3-(Phenylcyclobutyl)-1,2,4-triazoles were identified as inhibitors of 11 beta-Hydroxysteroid Dehydrogenase Type 1 (HSD1). They were shown to be active in the mouse in vivo pharmacodynamic model (PD) for HSD1 but exhibited a potent off-target activation of the Pregnane X Receptor (PXR). SAR studies and synthesis of analogs that led to the discovery of a selective HSD1 inhibitor are described in detail. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.125
• 作为产物：
  描述：

  4-溴-2-氯苯甲酸 在 硫酸 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 4-溴-2-氯苯肼
  参考文献：
  名称：

  5-芳基1,3,4-恶二唑-2-基硫代链烷酸：Rho /心肌相关转录因子（MRTF）/血清反应因子（SRF）介导的基因转录作为潜在抗纤维化剂的新型高效抑制剂用于硬皮病。

  摘要：

  通过使用血清反应元件荧光素酶启动子的表型高通量筛选，我们确定了Rho /心肌素相关转录因子（MRTF）/血清的新型5-芳基-1,3,4-恶二唑-2-基硫代丙酸铅抑制剂响应因子（SRF）介导的基因转录具有良好的效能（IC50 = 180 nM）。在清晰定义和协同作用的SAR的指导下，我们能够将细胞效能快速提高5个数量级。SAR的强大效能和深度，以及该系列相对较低的分子量，表明但不证明与未知分子靶标的结合可能是通过共价机制发生的。然而，该系列在高达100μM的浓度下没有可观察到的细胞毒性。

  DOI：

  10.1021/acs.jmedchem.8b01772

文献信息

• THIAZEPINE DERIVATIVE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2119719A1

  公开（公告）日：2009-11-18

  The present invention relates to a thiazepine derivative or a pharmacologically acceptable salt thereof having an excellent effect of inhibiting 11β-hydroxysteroid dehydrogenase type 1. A thiazepine derivative or a pharmacologically acceptable salt thereof having general formula (I): wherein R1 represents a hydrogen atom, a C1-C6 alkyl group or the like; R2 represents a C1-C6 alkyl group, a C1-C6 halogenated alkyl group, a C1-C6 hydroxyalkyl group, or the like; R3 represents a hydrogen atom or a C1-C6 alkyl group; R4 represents a C6-C10 aryl group that may be substituted with 1 to 5 group(s) independently selected from Substituent Group a or a heterocyclic group that may be substituted with 1 to 3 group(s) independently selected from Substituent Group a; Substituent Group a consists of a halogen atom, a C1-C6 alkyl group, a C6-C10 aryl group that may be substituted with 1 to 5 group(s) independently selected from Substituent Group b, and so forth; Substituent Group b consists of a halogen atom, a C1-C6 alkyl group, a C1-C6 halogenated alkyl group, and so forth.

  本发明涉及一种噻吩啶衍生物或其药理学上可接受的盐，具有优异的抑制11β-羟基类固醇脱氢酶1型的作用。具有通式（I）的噻吩啶衍生物或其药理学上可接受的盐： 其中 R1代表氢原子、C1-C6烷基或类似物；R2代表C1-C6烷基、C1-C6卤代烷基、C1-C6羟基烷基或类似物；R3代表氢原子或C1-C6烷基；R4代表可能被1至5个独立选择自取代基团a的基团取代的C6-C10芳基，或可能被1至3个独立选择自取代基团a的基团取代的杂环基团；取代基团a由卤原子、C1-C6烷基、可能被1至5个独立选择自取代基团b的基团取代的C6-C10芳基等组成；取代基团b由卤原子、C1-C6烷基、C1-C6卤代烷基等组成。
• The rapid preparation of 2-aminosulfonamide-1,3,4-oxadiazoles using polymer-supported reagents and microwave heating
  作者：Ian R. Baxendale、Steven V. Ley、Marisa Martinelli

  DOI：10.1016/j.tet.2005.03.062

  日期：2005.5

  Herein, we report on the preparation of a library of 5-substituted-2-amino-1,3,4-oxadiazoles and the corresponding thiadiazole analogues. Presented is a one-pot preparation of the 2-ammosulfonylated analogues through a three component coupling of an acylhydrazine, an isocyanate and sulfonyl chloride promoted by a polymer-supported phosphazine base under microwave dielectric heating. Also described is the optimization process and details pertaining to the elucidation of the reaction products. (c) 2005 Elsevier Ltd. All rights reserved.
• Substituted phenyl triazoles as selective inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1
  作者：Wanying Sun、Milana Maletic、Steven S. Mundt、Kashmira Shah、Hratch Zokian、Kathy Lyons、Sherman T. Waddell、James Balkovec

  DOI：10.1016/j.bmcl.2011.01.125

  日期：2011.4

  3-(Phenylcyclobutyl)-1,2,4-triazoles were identified as inhibitors of 11 beta-Hydroxysteroid Dehydrogenase Type 1 (HSD1). They were shown to be active in the mouse in vivo pharmacodynamic model (PD) for HSD1 but exhibited a potent off-target activation of the Pregnane X Receptor (PXR). SAR studies and synthesis of analogs that led to the discovery of a selective HSD1 inhibitor are described in detail. (C) 2011 Elsevier Ltd. All rights reserved.
• 5-Aryl-1,3,4-oxadiazol-2-ylthioalkanoic Acids: A Highly Potent New Class of Inhibitors of Rho/Myocardin-Related Transcription Factor (MRTF)/Serum Response Factor (SRF)-Mediated Gene Transcription as Potential Antifibrotic Agents for Scleroderma
  作者：Dylan J. Kahl、Kim M. Hutchings、Erika Mathes Lisabeth、Andrew J. Haak、Jeffrey R. Leipprandt、Thomas Dexheimer、Dinesh Khanna、Pei-Suen Tsou、Phillip L. Campbell、David A. Fox、Bo Wen、Duxin Sun、Marc Bailie、Richard R. Neubig、Scott D. Larsen

  DOI：10.1021/acs.jmedchem.8b01772

  日期：2019.5.9

  Through a phenotypic high-throughput screen using a serum response element luciferase promoter, we identified a novel 5-aryl-1,3,4-oxadiazol-2-ylthiopropionic acid lead inhibitor of Rho/myocardin-related transcription factor (MRTF)/serum response factor (SRF)-mediated gene transcription with good potency (IC50 = 180 nM). We were able to rapidly improve the cellular potency by 5 orders of magnitude

  通过使用血清反应元件荧光素酶启动子的表型高通量筛选，我们确定了Rho /心肌素相关转录因子（MRTF）/血清的新型5-芳基-1,3,4-恶二唑-2-基硫代丙酸铅抑制剂响应因子（SRF）介导的基因转录具有良好的效能（IC50 = 180 nM）。在清晰定义和协同作用的SAR的指导下，我们能够将细胞效能快速提高5个数量级。SAR的强大效能和深度，以及该系列相对较低的分子量，表明但不证明与未知分子靶标的结合可能是通过共价机制发生的。然而，该系列在高达100μM的浓度下没有可观察到的细胞毒性。