2-amino-4-chloro-γ-chlorobutyrophenone | 64605-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-4-chloro-γ-chlorobutyrophenone
• 英文别名: 4-Chlor-2-amino-y-chlorbutyrophenon；1-(2-Amino-4-chlorophenyl)-4-chlorobutan-1-one
• CAS: 64605-33-0
• 化学式: C₁₀H₁₁Cl₂NO
• 分子量: 232.109
• InChiKey: UMYRQEFGVURWIA-UHFFFAOYSA-N

物化性质

• 沸点：
  396.5±32.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-4-chloro-γ-chlorobutyrophenone 在 盐酸 、 sodium azide 、 sodium hydride 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis and Biological Evaluation of an Indazole-Based Selective Protein Arginine Deiminase 4 (PAD4) Inhibitor

  摘要：

  Protein arginine deiminase 4 (PAD4) is a calcium-dependent enzyme that catalyzes the conversion of arginine to citrulline within target proteins. Dysregulation of PAD4 has been implicated in a number of human diseases, including rheumatoid arthritis and other inflammatory diseases as well as cancer. In this study, we report on the design, synthesis, and evaluation of a new class of haloacetamidine-based compounds as potential PAD4 inhibitors. Specifically, we describe the identification of 4,5,6-trichloroindazole 24 as a highly potent PAD4 inhibitor that displays >10-fold selectivity for PAD4 over PAD3 and >50-fold over PAD1 and PAD2. The efficacy of this compound in cells was determined by measuring the inhibition of PAD4-mediated H4 citrullination in HL-60 granulocytes.

  DOI：

  10.1021/acsmedchemlett.8b00283
• 作为产物：
  描述：

  4-氯丁腈 、 3-氯苯胺 在 三氯化铝 、 三氯化硼 作用下， 生成 2-amino-4-chloro-γ-chlorobutyrophenone
  参考文献：
  名称：

  Sasakura, Kazuyuki; Kawasaki, Akiko; Sugasawa, Tsutomu, Synthetic Communications, 1988, vol. 18, # 3, p. 259 - 264

  摘要：

  DOI：

文献信息

• Novel, highly potent, selective 5-HT2A/D2 receptor antagonists as potential atypical antipsychotics
  作者：Taekyu Lee、Albert J Robichaud、Kristopher E Boyle、Yimin Lu、David W Robertson、Keith J Miller、Larry W Fitzgerald、John F McElroy、Brian L Largent

  DOI：10.1016/s0960-894x(02)01028-4

  日期：2003.2

  The discover of N-substituted-pyridoindolines and their binding affinities at the 5-HT2A, 5-HT2C and D-2 receptors, and in vivo efficacy as 5-HT2A antagonists is described. The structure-activity relationship of a series of core tetracyclic derivatives with varying butyrophenone sidechains is also discussed. This study has led to the identification of potent, orally bioavailable 5-HT2A/D2 receptor dual antagonists as potential atypical antipsychotics. (C) 2003 Elsevier Science Ltd. All rights reserved.
• SASAKURA, KAZUYUKI;KAWASAKI, AKIKO;SUGASAWA, TSUTOMU, SYNTH. COMMUN., 18,(1988) N 3, 259-264
  作者：SASAKURA, KAZUYUKI、KAWASAKI, AKIKO、SUGASAWA, TSUTOMU

  DOI：——

  日期：——
• SUBSTITUTED HETEROCYCLE FUSED GAMMA-CARBOLINES
  申请人：Bristol-Myers Squibb Pharma Company

  公开号：EP1192165A2

  公开（公告）日：2002-04-03
• US6713471B1
  申请人：——

  公开号：US6713471B1

  公开（公告）日：2004-03-30
• USRE39679E1
  申请人：——

  公开号：USRE39679E1

  公开（公告）日：2007-06-05