(R)-tert-butyl 4-benzamido-2-(N-isopropoxybiphenyl-4-ylsulfonamido)butanoate | 1061742-79-7

• 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: (R)-tert-butyl 4-benzamido-2-(N-isopropoxybiphenyl-4-ylsulfonamido)butanoate
• CAS: 1061742-79-7
• 化学式: C₃₀H₃₆N₂O₆S
• 分子量: 552.692
• InChiKey: TZJLWEMPURYCJE-HHHXNRCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  102.01
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 4-benzamido-2-(N-isopropoxybiphenyl-4-ylsulfonamido)butanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以99%的产率得到(R)-4-benzamido-2-(N-isopropoxybiphenyl-4-ylsulfonamido)-butanoic acid
  参考文献：
  名称：

  N-O-Isopropyl Sulfonamido-Based Hydroxamates as Matrix Metalloproteinase Inhibitors: Hit Selection and in Vivo Antiangiogenic Activity

  摘要：

  Matrix metalloproteinases (MMPs) have been shown to be involved in tumor-induced angiogenesis. In particular, MMP-2, MMP-9, and MMP-14 have been reported to be crucial for tumor angiogenesis and the formation of metastasis, thus becoming attractive targets in cancer therapy. Here, we report our optimization effort to identify novel N-isopropoxy-arylsulfonamide hydroxamates with improved inhibitory activity toward MMP-2, MMP-9, and MMP-14 with respect to the previously discovered compound 1. A new series of hydroxamates was designed, synthesized, and tested for their antiangiogenic activity using in vitro assays with human umbilical vein endothelial cells (HUVECs). A nanomolar MMP-2, MMP-9, and MMP-14 inhibitor was identified, compound 3, able to potently inhibit angiogenesis in vitro and also in vivo in the matrigel sponge assay in mice. Finally, X-ray crystallographic and docking studies were conducted for compound 3 in order to investigate its binding mode to MMP-9 and MMP-14.

  DOI：

  10.1021/acs.jmedchem.5b00367
• 作为产物：
  描述：

  (R)-tert-butyl 8-(biphenyl-4-ylsulfonyl)-10-methyl-3-oxo-1-phenyl-2,9-dioxa-4,8-diazaundecane-7-carboxylate 在 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 (R)-tert-butyl 4-benzamido-2-(N-isopropoxybiphenyl-4-ylsulfonamido)butanoate
  参考文献：
  名称：

  Diagnostic agents selective against metalloproteases

  摘要：

  该发明涉及具有亲和力针对金属蛋白酶MMP的芳基磺胺基化合物，其具有如下式(I)中所示的结构，其中R、R1、R2、R3、G和n具有规范中报告的含义，适当地标记有诊断成像团或甚至放射治疗团。该发明还涉及它们的制备方法，包括它们的药物组合物和它们作为诊断成像剂或放射治疗剂的用途。

  公开号：

  US09480758B2

文献信息

• ARYL-SULPHONAMIDIC DIMERS AS METALLOPROTEASES INHIBITORS
  申请人：Bracco Imaging S.p.A

  公开号：EP2149568A1

  公开（公告）日：2010-02-03

  The invention relates to dimeric aryl-sulphonamido compounds endowed with inhibitory activity against metalloproteases MMP, having formula (I) below          (M)-L-(M')     (I) wherein M and M', the same or different from each other, represent the residues of the mctalloprotcascs inhibitors of formula (II) wherein R, R1, R2, R3, G and n have the meanings reported in the specification; the invention also refers to the process for their preparation, to pharmaceutical compositions comprising them and to their use as therapeutic agents, particularly in the treatment of degenerative disorders.

  该发明涉及具有对金属蛋白酶MMP具有抑制活性的二聚芳基磺胺基化合物，其具有以下式(I)：(M)-L-(M')，其中M和M'，相同或不同，代表具有以下式(II)金属蛋白酶抑制剂的残基，其中R、R1、R2、R3、G和n在说明书中有所述；该发明还涉及其制备方法，包括它们的药物组合物以及它们作为治疗剂的用途，特别是在治疗退行性疾病方面。
• Compounds having aryl-sulphonamidic structure useful as metalloproteases inhibitors
  申请人：Bracco S.P.A.

  公开号：EP1972617A1

  公开（公告）日：2008-09-24

  The invention relates to aryl-sulphonamido compounds endowed with inhibitory activity against metallo proteases MMP, having formula (I) below wherein R, R1, R2, R3, R4, R5, n and m have the meanings reported in the specification; the invention also refers to the process for their preparation, to pharmaceutical compositions comprising them and to their use as therapeutic agents, particularly in the treatment of degenerative disorders.

  本发明涉及具有对金属蛋白酶MMP具有抑制活性的芳基磺胺基化合物，其具有以下式（I）其中R、R1、R2、R3、R4、R5、n和m具有规范中报告的含义；本发明还涉及它们的制备方法，包括它们的制药组合物以及它们作为治疗剂的用途，特别是在治疗退行性疾病方面。