3-(4-(4-(1-n-Propyl)phenyl)butanoyl)-4(S)-phenylmethyl-2-oxazolidinone | 162734-31-8

• 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: 3-(4-(4-(1-n-Propyl)phenyl)butanoyl)-4(S)-phenylmethyl-2-oxazolidinone
• 英文别名: (4S)-4-benzyl-3-[4-(4-propylphenyl)butanoyl]-1,3-oxazolidin-2-one
• CAS: 162734-31-8
• 化学式: C₂₃H₂₇NO₃
• 分子量: 365.472
• InChiKey: XJFZUUCNBKMHAO-NRFANRHFSA-N

物化性质

• 沸点：
  541.5±29.0 °C(predicted)
• 密度：
  1.142±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  3-(4-(4-(1-n-Propyl)phenyl)butanoyl)-4(S)-phenylmethyl-2-oxazolidinone 在 lithium hydroxide 、 Ti(OiPr)Cl3 、 双氧水 、 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 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (R)-4-((S)-3-Methyl-1-phenylcarbamoyl-butylcarbamoyl)-6-(4-propyl-phenyl)-hexanoic acid tert-butyl ester
  参考文献：
  名称：

  Orally active inhibitors of stromelysin-1 (MMP-3)

  摘要：

  Further development of N-carboxyalkyl dipeptide inhibitors of stromelysin-l (MMP-3) led to the discovery of C-carboxyalkyl dipeptide analogs with improved oral bioavailability. An in vivo assay of human MMP-3 mediated degradation of a macromolecular substrate in an extravascular space is described and inhibition studies are reported. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00109-6
• 作为产物：
  描述：

  4-氧代-4-(4-丙苯基)丁酸 在 palladium hydroxide - carbon 正丁基锂 、 草酰氯 、 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 3-(4-(4-(1-n-Propyl)phenyl)butanoyl)-4(S)-phenylmethyl-2-oxazolidinone
  参考文献：
  名称：

  Orally active inhibitors of stromelysin-1 (MMP-3)

  摘要：

  Further development of N-carboxyalkyl dipeptide inhibitors of stromelysin-l (MMP-3) led to the discovery of C-carboxyalkyl dipeptide analogs with improved oral bioavailability. An in vivo assay of human MMP-3 mediated degradation of a macromolecular substrate in an extravascular space is described and inhibition studies are reported. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00109-6

文献信息

• The design, synthesis, and structure-activity relationships of a series of macrocyclic MMP inhibitors
  作者：Douglas H. Steinman、Michael L. Curtin、Robert B. Garland、Steven K. Davidsen、H.Robin Heyman、James H. Holms、Daniel H. Albert、Terry J. Magoc、Ildiko B. Nagy、Patrick A. Marcotte、Junling Li、Douglas W. Morgan、Charles Hutchins、James B. Summers

  DOI：10.1016/s0960-894x(98)00396-5

  日期：1998.8

  A series of succinate-derived hydroxamic acids incorporating a macrocyclic ring were designed, synthesized, and evaluated as inhibitors of matrix metalloproteinases. The inhibitors were designed based on the published X-ray crystal structure of batimastat (1) complexed with human neutrophil collagenase (MMP-8). The synthesized compounds were shown to inhibit selected MMPs in vitro with low nanomolar

  设计，合成并评估了一系列掺入大环的琥珀酸酯衍生的异羟肟酸，并将其评估为基质金属蛋白酶的抑制剂。抑制剂是根据已公布的与人嗜中性粒细胞胶原酶（MMP-8）结合的巴马司他（1）的X射线晶体结构设计的。合成的化合物显示出可在体外以低纳摩尔浓度抑制选定的MMP。
• Carboxy-peptidyl derivatives as antidegenerative active agents
  申请人：Merck & Co., Inc.

  公开号：US05672583A1

  公开（公告）日：1997-09-30

  Novel Carboxy-peptidyl compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophobic epidermolysis bullosa, coronary thrombosis associated with atherosclerotic plaque rupture, and aneurysmal aortic disease. The matrix metalloendoproteinases are a family of zinc-containing proteinases including but not limited to stromelysin, collagenase, and gelatinase, that are capable of degrading the major components of articular cartilage and basement membranes. The inhibitors claimed herein may also be useful in preventing the pathological sequelae following a traumatic injury that could lead to a permanent disability. These compounds may also have utility as a means for birth control by preventing ovulation or implantation. ##STR1##

  化学式I的新型羧肽化合物被发现可用作基质金属蛋白酶介导的疾病的抑制剂，包括骨关节炎、风湿性关节炎、脓毒性关节炎、某些癌症中的肿瘤侵袭、牙周病、角膜溃疡、蛋白尿、皮肤萎缩性表皮溃疡病、动脉粥样硬化斑块破裂引起的冠状动脉血栓形成以及动脉瘤性主动脉疾病。基质金属蛋白酶是一类含锌蛋白酶家族，包括但不限于基质金属蛋白酶、胶原酶和明胶酶，能够降解关节软骨和基底膜的主要成分。本声明的抑制剂也可能有助于预防因外伤而导致的病理性后遗症，可能导致永久残疾。这些化合物也可能作为一种避孕手段，通过阻止排卵或着床来实现。
• EP0671911A4
  申请人：——

  公开号：EP0671911A4

  公开（公告）日：1996-08-21
• CARBOXY-PEPTIDYL DERIVATIVES AS ANTIDEGENERATIVE ACTIVE AGENTS
  申请人：MERCK & CO. INC.

  公开号：EP0671911A1

  公开（公告）日：1995-09-20
• US5672583A
  申请人：——

  公开号：US5672583A

  公开（公告）日：1997-09-30