N-acetyl-β-(4-methoxyphenylsulfonyl)-D,L-alanine methyl ester | 202666-32-8

• 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: N-acetyl-β-(4-methoxyphenylsulfonyl)-D,L-alanine methyl ester
• 英文别名: N-acetyl-beta-(4-methoxyphenylsulfonyl)-D,L-alanine methyl ester；methyl 2-acetamido-3-(4-methoxyphenyl)sulfonylpropanoate
• CAS: 202666-32-8
• 化学式: C₁₃H₁₇NO₆S
• 分子量: 315.347
• InChiKey: RBKBKPBIJNSWKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-acetyl-β-(4-methoxyphenylsulfonyl)-D,L-alanine methyl ester 在 盐酸 、 溶剂黄146 作用下， 生成 2-Amino-3-(4-methoxyphenyl)sulfonylpropanoic acid
  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-acetamido-3-(4-methoxyphenylsulfanyl)propionic acid methyl ester 在 Oxone 作用下， 生成 N-acetyl-β-(4-methoxyphenylsulfonyl)-D,L-alanine methyl ester
  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

• Thiol sulfone metalloprotease inhibitors
  申请人：Monsanto Company

  公开号：US06013649A1

  公开（公告）日：2000-01-11

  This invention is directed to proteinase (protease) inhibitors, and more particularly to thiol sulfone inhibitors for matrix metalloproteinase 13(MMP-13), compositions of proteinase inhibitors, intermediates for the syntheses of proteinase inhibitors, processes for the preparation of proteinase inhibitors and processes for treating pathological conditions associated with pathological matrix metalloproteinase activity related to MMP-13.

  这项发明涉及蛋白酶（蛋白酶）抑制剂，更具体地涉及巯基磺酮抑制剂用于基质金属蛋白酶13（MMP-13），蛋白酶抑制剂的组合物，蛋白酶抑制剂合成的中间体，制备蛋白酶抑制剂的方法以及用于治疗与MMP-13相关的病理基质金属蛋白酶活性相关的病理状况的方法。
• THIOL SULFONE METALLOPROTEASE INHIBITORS
  申请人：MONSANTO COMPANY

  公开号：EP0939628B1

  公开（公告）日：2003-03-05
• US6013649A
  申请人：——

  公开号：US6013649A

  公开（公告）日：2000-01-11
• 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.