(4S)-4-benzyl-3-[(2S)-2-(cyclopropylmethyl)pent-4-enoyl]-1,3-oxazolidin-2-one | 909717-43-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-4-benzyl-3-[(2S)-2-(cyclopropylmethyl)pent-4-enoyl]-1,3-oxazolidin-2-one
• 英文别名: (S)-4-Benzyl-3-((S)-2-cyclopropylmethyl-pent-4-enoyl)-oxazolidin-2-one
• CAS: 909717-43-7
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: VCJVZKZDEZOTAF-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-4-benzyl-3-[(2S)-2-(cyclopropylmethyl)pent-4-enoyl]-1,3-oxazolidin-2-one 在 N-羟基-7-氮杂苯并三氮唑 、 过氧化氢,锂盐(1:1) 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-2-Cyclopropylmethyl-pent-4-enoic acid 3,5-bis-trifluoromethyl-benzylamide
  参考文献：
  名称：

  4-Amino-2-alkyl-butyramides as small molecule CCR2 antagonists with favorable pharmacokinetic properties

  摘要：

  A systematic examination of the central aromatic portion of the lead (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-(4-fluorophenyl)-4-(1'H-spiro[indene-1,4'-piperidin]-1'-yl)butanamide (9) led to the discovery of a novel class of CCR2 receptor antagonists, which carry small alicyclic groups such as cyclopropyl, cylobutyl, or cyclopropylmethyl attached at C-2 of the carbon backbone. The most potent compound discovered, namely (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-cyclopropyl-4-[(1R,3'R)-3'-methyl-1'H-spiro[indene-1,4'-piperidin]-1'-yl]butanamide (29), showed very high binding affinity (IC50 = 4 nM, human monocyte) and excellent selectivity toward other related chemokine receptors. The excellent pharmacokinetic profile of this new lead compound allows for extensive in vivo evaluation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.011
• 作为产物：
  描述：

  (S)-4-苄基-3-(戊-4-烯酰基)恶唑烷-2-酮 在 palladium diacetate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 (4S)-4-benzyl-3-[(2S)-2-(cyclopropylmethyl)pent-4-enoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  4-Amino-2-alkyl-butyramides as small molecule CCR2 antagonists with favorable pharmacokinetic properties

  摘要：

  A systematic examination of the central aromatic portion of the lead (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-(4-fluorophenyl)-4-(1'H-spiro[indene-1,4'-piperidin]-1'-yl)butanamide (9) led to the discovery of a novel class of CCR2 receptor antagonists, which carry small alicyclic groups such as cyclopropyl, cylobutyl, or cyclopropylmethyl attached at C-2 of the carbon backbone. The most potent compound discovered, namely (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-cyclopropyl-4-[(1R,3'R)-3'-methyl-1'H-spiro[indene-1,4'-piperidin]-1'-yl]butanamide (29), showed very high binding affinity (IC50 = 4 nM, human monocyte) and excellent selectivity toward other related chemokine receptors. The excellent pharmacokinetic profile of this new lead compound allows for extensive in vivo evaluation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.011

文献信息

• MACROCYCLIC INHIBITORS OF FLAVIVIRIDAE VIRUSES
  申请人：Selcia Ltd.

  公开号：US20140030221A1

  公开（公告）日：2014-01-30

  Provided are compounds of Formula I: and pharmaceutically acceptable salts and esters thereof. The compounds, compositions, and methods provided are useful for the treatment of virus infections, particularly hepatitis C infections.

  提供了I式化合物及其药学上可接受的盐和酯。所提供的化合物、组合物和方法对于治疗病毒感染，特别是丙型肝炎感染具有有用性。
• Macrocyclic inhibitors of flaviviridae viruses
  申请人：Gilead Sciences, Inc.

  公开号：US09145441B2

  公开（公告）日：2015-09-29

  Provided are compounds of Formula I: and pharmaceutically acceptable salts and esters thereof. The compounds, compositions, and methods provided are useful for the treatment of virus infections, particularly hepatitis C infections.

  所提供的是I式化合物及其药学上可接受的盐和酯。所提供的化合物、组合物和方法对于治疗病毒感染，特别是丙型肝炎感染，是有用的。
• [EN] COMPOUND CONTAINING CYCLOALKYL OR HALOALKYL<br/>[FR] COMPOSÉ CONTENANT CYCLOALKYLE OU HALOALKYLE<br/>[ZH] 含有环烷基或卤代烷基的化合物
  申请人：[en]CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.;[zh]正大天晴药业集团股份有限公司

  公开号：WO2023098730A1

  公开（公告）日：2023-06-08

  本公开涉及含有环烷基或卤代烷基的化合物，具体公开了式I"所示化合物、其立体异构体或其药学上可接受的盐，其制备方法，含有该化合物的药物组合物，及其治疗肿瘤的用途。
• US9145441B2
  申请人：——

  公开号：US9145441B2

  公开（公告）日：2015-09-29
• US9512175B2
  申请人：——

  公开号：US9512175B2

  公开（公告）日：2016-12-06