{4-[4-(Piperidin-1-ylcarbonyl)-oxazol-2-yl]-benzyl}-carbamic acid tert-butyl ester | 622847-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: {4-[4-(Piperidin-1-ylcarbonyl)-oxazol-2-yl]-benzyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[[4-[4-(piperidine-1-carbonyl)-1,3-oxazol-2-yl]phenyl]methyl]carbamate
• CAS: 622847-22-7
• 化学式: C₂₁H₂₇N₃O₄
• 分子量: 385.463
• InChiKey: QPPRQKVOBCDWRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {4-[4-(Piperidin-1-ylcarbonyl)-oxazol-2-yl]-benzyl}-carbamic acid tert-butyl ester 在 盐酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[[4-[4-(piperidine-1-carbonyl)-1,3-oxazol-2-yl]phenyl]methyl]-2-pyridin-2-ylacetamide
  参考文献：
  名称：

  Discovery and structure–activity relationship of 2-phenyl-oxazole-4-carboxamide derivatives as potent apoptosis inducers

  摘要：

  As a continuation of our efforts to discover novel apoptosis inducers as anticancer agents using a cell-based caspase HTS assay, 2-phenyl-oxazole-4-carboxamide derivatives were identified. The structure-activity relationships of this class of molecules were explored. Compound 1k, with EC50 of 270 nM and GI(50) of 229 nM in human colorectal DLD-1 cells, was selected and demonstrated the ability to cleave PARP and displayed DNA laddering, the hallmarks of apoptosis. Compound 1k showed 63% tumor growth inhibition in human colorectal DLD-1 xenograft mouse model at 50 mpk, bid. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.018
• 作为产物：
  描述：

  4-[(叔丁氧羰基氨基)甲基]苯甲酸 在 lithium hydroxide 、 伯吉斯试剂 、 三氯溴甲烷 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 {4-[4-(Piperidin-1-ylcarbonyl)-oxazol-2-yl]-benzyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Discovery and structure–activity relationship of 2-phenyl-oxazole-4-carboxamide derivatives as potent apoptosis inducers

  摘要：

  As a continuation of our efforts to discover novel apoptosis inducers as anticancer agents using a cell-based caspase HTS assay, 2-phenyl-oxazole-4-carboxamide derivatives were identified. The structure-activity relationships of this class of molecules were explored. Compound 1k, with EC50 of 270 nM and GI(50) of 229 nM in human colorectal DLD-1 cells, was selected and demonstrated the ability to cleave PARP and displayed DNA laddering, the hallmarks of apoptosis. Compound 1k showed 63% tumor growth inhibition in human colorectal DLD-1 xenograft mouse model at 50 mpk, bid. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.018

文献信息

• Novel phenyl derivatives as inducers of apoptosis
  申请人：Cai Xiong Sui

  公开号：US20050026929A1

  公开（公告）日：2005-02-03

  The present invention related to certain phenyl derivatives that are activators of caspases and inducers of apoptosis, pharmaceutical composition comprising these compounds and method of treating cancer utilizing these compounds.

  本发明涉及某些苯基衍生物，它们是caspases的激活剂和凋亡诱导剂，包括这些化合物的制药组合物以及利用这些化合物治疗癌症的方法。
• [EN] NOVEL PHENYL DERIVATIVES AS INDUCERS OF APOPTOSIS<br/>[FR] NOUVEAUX DERIVES DE PHENYLE INDUCTEURS D'APOPTOSE
  申请人：AXYS PHARM INC

  公开号：WO2003090680A2

  公开（公告）日：2003-11-06

  The present invention related to certain phenyl derivatives that are activators of caspases and inducers of apoptosis, pharmaceutical composition comprising these compounds and method of treating cancer utilizing these compounds.
• Discovery and structure–activity relationship of 2-phenyl-oxazole-4-carboxamide derivatives as potent apoptosis inducers
  作者：Vincent W.-F. Tai、David Sperandio、Emma J. Shelton、Joane Litvak、Keith Pararajasingham、Ben Cebon、Julia Lohman、John Eksterowicz、Seema Kantak、Peter Sabbatini、Cindy Brown、Jennifer Zeitz、Chris Reed、Bill Maske、Doris Graupe、Alberto Estevez、Jason Oeh、Darren Wong、Yong Ni、Paul Sprengeler、Robert Yee、Catherine Magill、Anthony Neri、Sui Xiong Cai、John Drewe、Ling Qiu、John Herich、Ben Tseng、Shailaja Kasibhatla、Jeffrey R. Spencer

  DOI：10.1016/j.bmcl.2006.06.018

  日期：2006.9

  As a continuation of our efforts to discover novel apoptosis inducers as anticancer agents using a cell-based caspase HTS assay, 2-phenyl-oxazole-4-carboxamide derivatives were identified. The structure-activity relationships of this class of molecules were explored. Compound 1k, with EC50 of 270 nM and GI(50) of 229 nM in human colorectal DLD-1 cells, was selected and demonstrated the ability to cleave PARP and displayed DNA laddering, the hallmarks of apoptosis. Compound 1k showed 63% tumor growth inhibition in human colorectal DLD-1 xenograft mouse model at 50 mpk, bid. (c) 2006 Elsevier Ltd. All rights reserved.