2-(Acetylamino)-3-[[4-(phenylthio)phenyl]sulfonyl]-N-[(3,4,5,6-tetrahydro-2H-pyran-2-yl]oxy]propanamide | 310464-05-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(Acetylamino)-3-[[4-(phenylthio)phenyl]sulfonyl]-N-[(3,4,5,6-tetrahydro-2H-pyran-2-yl]oxy]propanamide
• 英文别名: 2-acetamido-N-(oxan-2-yloxy)-3-(4-phenylsulfanylphenyl)sulfonylpropanamide
• CAS: 310464-05-2
• 化学式: C₂₂H₂₆N₂O₆S₂
• 分子量: 478.59
• InChiKey: RSWBKBGOXSGNGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(Acetylamino)-3-[[4-(phenylthio)phenyl]sulfonyl]-N-[(3,4,5,6-tetrahydro-2H-pyran-2-yl]oxy]propanamide 在 甲醇 、 对甲苯磺酸 作用下， 生成 2-(Acetylamino)-N-hydroxy-3-[[4-(phenylthio)phenyl]sulfonyl]propanamide
  参考文献：
  名称：

  α-Amino-β-sulphone hydroxamates as potent MMP-13 inhibitors that spare MMP-1

  摘要：

  A series of alpha -amino-beta -sulphone hydroxamates was prepared and evaluated for potency versus MMP-13 and selectivity versus MMP-1. Various substituents were employed on the alpha -amino group (P-1 position), as well as different groups attached to the sulphone group extending into P-1'. Low nanomolar potency was obtained for MMP-13 with selectivity versus MMP-1 of > 1000x for a number of analogues. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00556-x
• 作为产物：
  描述：

  2-乙酰胺基丙烯酸甲酯 在 盐酸 、 Oxone 、 potassium carbonate 、 1-羟基苯并三唑 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(Acetylamino)-3-[[4-(phenylthio)phenyl]sulfonyl]-N-[(3,4,5,6-tetrahydro-2H-pyran-2-yl]oxy]propanamide
  参考文献：
  名称：

  α-Amino-β-sulphone hydroxamates as potent MMP-13 inhibitors that spare MMP-1

  摘要：

  A series of alpha -amino-beta -sulphone hydroxamates was prepared and evaluated for potency versus MMP-13 and selectivity versus MMP-1. Various substituents were employed on the alpha -amino group (P-1 position), as well as different groups attached to the sulphone group extending into P-1'. Low nanomolar potency was obtained for MMP-13 with selectivity versus MMP-1 of > 1000x for a number of analogues. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00556-x

文献信息

• &agr;-amino-&bgr;-sulfonyl hydroxamic acid compounds
  申请人：G.D. Searle & Co.

  公开号：US06583299B1

  公开（公告）日：2003-06-24

  A family of molecules is disclosed that inhibit matrix metalloprotease (MMP) activity, and particularly inhibit the activity of one or more of MMP-2, MMP-9, or MMP-13, while generally exhibiting little activity against MMP-1. A contemplated compound also exhibits little inhibition of the production of TNF. A contemplated compound is an &agr;-amino-&bgr;-sulfonyl carbocyclo, heterocyclo, aryl, or heteroaryl hydroxamic acid. Also disclosed are processes for preparing a contemplated compound and for treating a mammal having a condition associated with pathological matrix metalloprotease activity.

  本发明揭示了一类分子，可抑制基质金属蛋白酶（MMP）活性，特别是抑制MMP-2、MMP-9或MMP-13中的一个或多个的活性，同时通常对MMP-1的活性表现较少。考虑到的化合物也表现出对TNF的产生很少的抑制作用。考虑到的化合物是α-氨基-β-磺酰基环烷、杂环、芳基或杂芳基羟肟酸。还揭示了制备考虑到的化合物和治疗与病理性基质金属蛋白酶活性相关的哺乳动物疾病的过程。
• ALPHA-AMINO-BETA-SULFONYL HYDROXAMIC ACID COMPOUNDS
  申请人：G.D. SEARLE & CO.

  公开号：EP1178959A1

  公开（公告）日：2002-02-13
• US6583299B1
  申请人：——

  公开号：US6583299B1

  公开（公告）日：2003-06-24
• [EN] DOLLAR G(A)-AMINO- DOLLAR G(B)-SULFONYL HYDROXAMIC ACID COMPOUNDS<br/>[FR] COMPOSES ACIDES DOLLAR G(A)-AMINO- DOLLAR G(B)-SULFONYLE HYDROXAMIQUES
  申请人：SEARLE & CO

  公开号：WO2000071514A1

  公开（公告）日：2000-11-30

  A family of molecules of formula (A) in which R1 is a 5- or 6-membered carbocyclo, heterocyclo, aryl or heteroaryl radical such that its size defined by certain parameters; R20 is -O-R?21, -NR13-O-R22 or -NR13-O-R14¿; and the other variables are as defined in the claims, is disclosed that inhibit matrix metalloproteinase (MMP) activity, and particularly inhibit the activity of one or more of MMP-2, MMP-9, or MMP-13, while generally exhibiting little activity against MMP-1. A contemplated compound also exhibits little inhibition of the production of TNF. Also disclosed are process for preparing a contemplated compound and for treating a mammal having a condition associated with pathological matrix metalloproteinase activity.
• α-Amino-β-sulphone hydroxamates as potent MMP-13 inhibitors that spare MMP-1
  作者：Daniel P Becker、Thomas E Barta、Louis Bedell、Gary DeCrescenzo、John Freskos、Daniel P Getman、Susan L Hockerman、Madeleine Li、Pramod Mehta、Brent Mischke、Grace E Munie、Craig Swearingen、Clara I Villamil

  DOI：10.1016/s0960-894x(01)00556-x

  日期：2001.10

  A series of alpha -amino-beta -sulphone hydroxamates was prepared and evaluated for potency versus MMP-13 and selectivity versus MMP-1. Various substituents were employed on the alpha -amino group (P-1 position), as well as different groups attached to the sulphone group extending into P-1'. Low nanomolar potency was obtained for MMP-13 with selectivity versus MMP-1 of > 1000x for a number of analogues. (C) 2001 Elsevier Science Ltd. All rights reserved.