benzyl-4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1-(triisopropylsilyl)-1H-pyrrol-3-yl]piperidin-4-ol | 321344-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: benzyl-4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1-(triisopropylsilyl)-1H-pyrrol-3-yl]piperidin-4-ol
• 英文别名: 4-(1-Benzyl-4-hydroxypiperidin-4-yl)-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1-triisopropylsilyl-1 H-pyrrole；4-(1-benzyl-4-hydroxypiperidin-4-yl)-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1-triisoprolpylsilyl-1H-pyrrole；4-(1-benzyl-4-hydroxypiperidin-4-yl)-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1-triisopropylsilyl-1H-pyrrole；1-benzyl-4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1-tri(propan-2-yl)silylpyrrol-3-yl]piperidin-4-ol
• CAS: 321344-89-2
• 化学式: C₃₆H₄₆FN₃OSi
• 分子量: 583.865
• InChiKey: ZZTWHFYBFOQIGY-UHFFFAOYSA-N

物化性质

• 沸点：
  641.7±55.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.86
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  41.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl-4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1-(triisopropylsilyl)-1H-pyrrol-3-yl]piperidin-4-ol 在 钯 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以to give 483 mg (yield 98%) of the title compound as a white amorphous solid的产率得到2-(4-fluorophenyl)-4-(4-hydroxypiperidin-4-yl)-3-(pyridin-4-yl)-1-triisopropylsilyl-1H-pyrrole
  参考文献：
  名称：

  Heteroaryl-substituted pyrrole derivatives, their preparation and their therapeutic uses

  摘要：

  具有对式（I)′的炎症细胞因子产生活性的化合物：1A′为吡咯；R1′为苯基或萘基；R2′为吡啶基或嘧啶基；R3′为（IIa)′，（IIb)′或（IIc)′；2m′为1；E′为氮；D′为>C(R5′)—，R5′为氢，取代基&agr;′或取代基&bgr;′；B′为含氮的5元杂环；R4′为取代基&agr;′、取代基&bgr;′和取代基&ggr;′中的1至3个取代基；R1′和R3′与吡咯相邻的两个原子连接到R2′与吡咯原子相结合；取代基&agr;′为羟基、硝基、氰基、卤素、烷氧基、卤代烷氧基、烷基硫基、卤代烷基硫基或—NRa′Rb′；Ra′和Rb′为氢、烷基、烯基、炔基、芳基烷基或烷基磺酰基，或Ra′和Rb′与氮原子形成杂环；取代基&bgr;′为烷基、烯基、炔基、芳基烷基或环烷基；取代基&ggr;′为氧代、羟肟、烷氧肟、烷基、烷基二氧、烷基亚磺酰基、烷基磺酰基、芳基、芳氧基、烷基亚甲基或芳基亚甲基。

  公开号：

  US20040054173A1
• 作为产物：
  描述：

  4-bromo-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1-triisopropylsilyl-1H-pyrrole 、 N-苄基哌啶酮 在 叔丁基锂 作用下， 以61%的产率得到benzyl-4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1-(triisopropylsilyl)-1H-pyrrol-3-yl]piperidin-4-ol
  参考文献：
  名称：

  Heteroaryl-substituted pyrrole derivates, their preparation and their therapeutic uses

  摘要：

  化合物的结构式（I）：[其中：A为吡咯环；R1为可选取代的苯或萘基团；R2为可选取代的吡啶或嘧啶基团；R3代表具有下述结构的基团-X-R4，其中X为单键或烯基链，R4为可选取代的含氮杂环基团；所选取自8-氮杂双环[3.2.1]辛烯基、9-氮杂双环[3.3.1]壬烯基和喹啉环基团，前提是所述取代基R1和R3连接到所述吡咯环的两个相邻原子，这两个原子与所述取代基R2连接的吡咯环原子相邻]具有出色的抑制炎症细胞因子产生活性。

  公开号：

  EP1243589A1

文献信息

• Heteroaryl-substituted pyrrole derivatives, their preparation and their therapeutic uses
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20040054173A1

  公开（公告）日：2004-03-18

  Compounds having activity against production of an inflammatory cytokine of formula (I)′: 1 A′ is pyrrole; R 1′ is phenyl or naphthyl; R 2′ is pyridyl or pyrimidinyl; R 3′ is (IIa)′, (IIb)′ or (IIc)′: 2 m′ is 1; E′ is nitrogen; D′ is >C(R 5′ )—, R 5′ is hydrogen, Substituent &agr;′ or Substituent &bgr;′; B′ is nitrogen-containing 5-membered heterocyclic; R 4′ is 1 to 3 substituents from Substituent &agr;′, Substituent &bgr;′ and Substituent &ggr;′; R 1′ and R 3′ are bonded to two atoms of the pyrrole adjacent to the pyrrole atom bonded to R 2′ ; Substituent &agr;′ is hydroxyl, nitro, cyano, halogen, alkoxy, halogeno alkoxy, alkylthio, halogeno alkylthio or —NR a′ R b′ ; R a′ and R b′ are hydrogen, alkyl, alkenyl, alkynyl, aralkyl or alkylsulfonyl, or R a′ and R b′ with the nitrogen atom form a heterocyclyl; Substituent &bgr;′ is alkyl, alkenyl, alkynyl, aralkyl or cycloalkyl; Substituent &ggr;′ is oxo, hydroxyimino, alkoxyimino, alkylene, alkylenedioxy, alkylsulfinyl, alkylsulfonyl, aryl, aryloxy, alkylidenyl or aralkylidenyl.

  具有对抗公式(I)′炎症细胞因子生成活性的化合物： 1 A′是吡咯；R 1′ 是苯基或萘基；R 2′ 是吡啶基或嘧啶基；R 3′ 是(IIa)′，(IIb)′或(IIc)′： 2 m′是1；E′是氮；D′是>C(R 5′ )—, R 5′ 是氢，取代基α′或取代基β′；B′是含氮的5-成员杂环；R 4′ 是来自取代基α′，取代基β′和取代基γ′的1至3个取代基；R 1′ 和R 3′ 分别与吡咯环上与R 2′ 相连的吡咯原子的两个相邻原子成键；取代基α′是羟基，硝基，氰基，卤素，烷氧基，卤代烷氧基，烷基亚砜，卤代烷基亚砜或—NR a′ R b′ ；R a′ 和R b′ 是氢，烷基，烯基，炔基，芳烷基或烷基亚磺酰基，或者R a′ 和R b′ 与氮原子形成杂环；取代基β′是烷基，烯基，炔基，芳烷基或环烷基；取代基γ′是氧代，羟基亚胺，烷氧基亚胺，亚烷基，亚烷基二氧，烷基亚磺酰基，烷基亚磺酰基，芳基，芳氧基，亚烷基或芳亚烷基。
• Heteroaryl-substituted pyrrole derivates, their preparation and their therapeutic uses
  申请人：Sankyo Company Limited

  公开号：EP1243589A1

  公开（公告）日：2002-09-25

  Compounds of formula (I): [wherein: A is a pyrrole ring; R1 is an optionally substituted phenyl or naphthyl group; R2 is an optionally substituted pyridyl or pyrimidinyl group; R3 represents a group of the formula -X-R4, wherein X is a single bond or an alkenylene group, and R4 is an optionally substituted nitrogen-containing heterocyclyl group; selected from the group consisting of 8-azabicyclo[3.2.1]octenyl, 9-azabicyclo[3.3.1]nonenyl and quinuclidinenyl groups, PROVIDED THAT said substituents R1 and R3 are bonded to the two atoms of said pyrrole ring which are adjacent to the atom of the pyrrole ring to which said substituent R2 is bonded] have excellent inhibitory activity against the production of inflammatory cytokines.

  化合物的结构式（I）：[其中：A为吡咯环；R1为可选取代的苯或萘基团；R2为可选取代的吡啶或嘧啶基团；R3代表具有下述结构的基团-X-R4，其中X为单键或烯基链，R4为可选取代的含氮杂环基团；所选取自8-氮杂双环[3.2.1]辛烯基、9-氮杂双环[3.3.1]壬烯基和喹啉环基团，前提是所述取代基R1和R3连接到所述吡咯环的两个相邻原子，这两个原子与所述取代基R2连接的吡咯环原子相邻]具有出色的抑制炎症细胞因子产生活性。
• EP1352906
  申请人：——

  公开号：——

  公开（公告）日：——
• Tetrahydropyridine derivatives with inhibitory activity on the production of proinflammatory cytokines: Part 1
  作者：Akira Nakao、Nobuyuki Ohkawa、Takayoshi Nagasaki、Takashi Kagari、Hiromi Doi、Takaichi Shimozato、Shigeru Ushiyama、Kazumasa Aoki

  DOI：10.1016/j.bmcl.2009.06.094

  日期：2009.8

  We investigated proinflammatory cytokine TNF alpha production inhibitors in order to develop novel anti-inflammatory agents. According to the results, we found that 17, a pyrrole derivative possessing a tetrahydropyridine group at the beta-position, showed potent inhibitory activity in vitro (inhibition of lipopolysaccharide (LPS) induced TNF alpha production in human whole blood, IC(50) = 1.86 mu M) and in vivo (inhibition of LPS induced TNF alpha production in mice, ID(50) = 5.98 mg/kg). Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.