tert-butyl {2-[(4-{3-fluoro-5-[(4-isopropylpiperazin-1-yl)methyl]pyridin-2-yl}benzoyl)amino]phenyl}carbamate | 900176-82-1

• 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: tert-butyl {2-[(4-{3-fluoro-5-[(4-isopropylpiperazin-1-yl)methyl]pyridin-2-yl}benzoyl)amino]phenyl}carbamate
• 英文别名: tert-butyl N-[2-[[4-[3-fluoro-5-[(4-propan-2-ylpiperazin-1-yl)methyl]pyridin-2-yl]benzoyl]amino]phenyl]carbamate
• CAS: 900176-82-1
• 化学式: C₃₁H₃₈FN₅O₃
• 分子量: 547.673
• InChiKey: PYFQSYQLSGDYDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  86.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl {2-[(4-{3-fluoro-5-[(4-isopropylpiperazin-1-yl)methyl]pyridin-2-yl}benzoyl)amino]phenyl}carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 N-(2-aminophenyl)-4-{3-fluoro-5-[(4-isopropylpiperazin-1-yl)methyl]pyridin-2-yl}benzamide
  参考文献：
  名称：

  Design and campaign synthesis of pyridine-based histone deacetylase inhibitors

  摘要：

  A lead benzamide, bearing a cyanopyridyl moiety (3), was identified as a potent and low molecular weight histone deacetylase ( HDAC) inhibitor. Various replacements of the cyano group were explored at the C3-position, along with the exploration of solubility-enhancing groups at the C5-position. It was determined that cyano substitution at the C3-position of the pyridyl core, along with a methylazetidinyl substituent at the C5-position yielded optimal HDAC1 inhibition and anti-proliferative activity in HCT-116 cells. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.058
• 作为产物：
  描述：

  1-异丙基哌嗪 、 反应 18.0h， 生成 tert-butyl {2-[(4-{3-fluoro-5-[(4-isopropylpiperazin-1-yl)methyl]pyridin-2-yl}benzoyl)amino]phenyl}carbamate
  参考文献：
  名称：

  Design and campaign synthesis of pyridine-based histone deacetylase inhibitors

  摘要：

  A lead benzamide, bearing a cyanopyridyl moiety (3), was identified as a potent and low molecular weight histone deacetylase ( HDAC) inhibitor. Various replacements of the cyano group were explored at the C3-position, along with the exploration of solubility-enhancing groups at the C5-position. It was determined that cyano substitution at the C3-position of the pyridyl core, along with a methylazetidinyl substituent at the C5-position yielded optimal HDAC1 inhibition and anti-proliferative activity in HCT-116 cells. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.058

文献信息

• N-PHENYL-4-PYRIDIN-2-YL-BENZAMIDE DERIVATIVES AS HISTONE DEACYLASE (HDAC) INHIBITORS FOR THE TREATMENT OF CANCER
  申请人：Gibson Keith Hopkinson

  公开号：US20100075942A1

  公开（公告）日：2010-03-25

  The invention concerns benzamide derivatives of Formula (I) wherein R 1a , R 1b , R 1c , R 2 , R 3 , R 4 , W, m and n have any of the meanings defined in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an antiproliferative agent in the prevention or treatment of tumours or other proliferative conditions which are sensitive to the inhibition of histone deacetylase (HDAC).

  本发明涉及公式（I）的苯甲酰胺衍生物，其中R1a、R1b、R1c、R2、R3、R4、W、m和n具有描述中定义的任何含义；它们的制备过程，含有它们的制药组合物以及它们在制造用作抗增殖剂的药物，用于预防或治疗对组蛋白去乙酰化酶（HDAC）抑制敏感的肿瘤或其他增殖性疾病。
• Design and campaign synthesis of pyridine-based histone deacetylase inhibitors
  作者：David M. Andrews、Keith M. Gibson、Mark A. Graham、Zbigniew S. Matusiak、Craig A. Roberts、Elaine S.E. Stokes、Madeleine C. Brady、Christine M. Chresta

  DOI：10.1016/j.bmcl.2008.03.058

  日期：2008.4

  A lead benzamide, bearing a cyanopyridyl moiety (3), was identified as a potent and low molecular weight histone deacetylase ( HDAC) inhibitor. Various replacements of the cyano group were explored at the C3-position, along with the exploration of solubility-enhancing groups at the C5-position. It was determined that cyano substitution at the C3-position of the pyridyl core, along with a methylazetidinyl substituent at the C5-position yielded optimal HDAC1 inhibition and anti-proliferative activity in HCT-116 cells. (c) 2008 Elsevier Ltd. All rights reserved.