4-benzylsulfanyl-2-[carboxymethyl-(4-methoxy-benzenesulfonyl)-amino]-butyric acid methyl ester | 237423-50-6

• 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: 4-benzylsulfanyl-2-[carboxymethyl-(4-methoxy-benzenesulfonyl)-amino]-butyric acid methyl ester
• 英文别名: 2-{[3-(Benzylsulphanyl)-1-(methoxycarbonyl)propyl]-[(4-methoxyphenyl)sulphonyl]amino}acetic acid；2-[(4-Benzylsulfanyl-1-methoxy-1-oxobutan-2-yl)-(4-methoxyphenyl)sulfonylamino]acetic acid
• CAS: 237423-50-6
• 化学式: C₂₁H₂₅NO₇S₂
• 分子量: 467.564
• InChiKey: JUNRFKOBCQDXIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-benzylsulfanyl-2-[carboxymethyl-(4-methoxy-benzenesulfonyl)-amino]-butyric acid methyl ester 在 氢氧化钾 、 双(2-氧代-3-恶唑烷基)次磷酰氯 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-[[(benzhydryl-carbamoyl)-methyl]-(4-methoxy-benzenesulfonyl)-amino]-4-benzylsulfanyl-butyric acid
  参考文献：
  名称：

  Picking the S1, S1′ and S2′ pockets of matrix metalloproteinases. A niche for potent acyclic sulfonamide inhibitors

  摘要：

  A series of acyclic hydroxamic acids harboring strategically placed alpha-arylsulfonamido and thioether groups was synthesized and found to be potent inhibitors of various MMPs. An unprecedented cleavage of t-butyl hydroxamates to hydroxamic acids was found. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00259-0
• 作为产物：
  描述：

  4-benzylsulfanyl-2-[tert-butoxycarbonylmethyl-(4-methoxy-benzenesulfonyl)-amino]-butyric acid methyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以68%的产率得到4-benzylsulfanyl-2-[carboxymethyl-(4-methoxy-benzenesulfonyl)-amino]-butyric acid methyl ester
  参考文献：
  名称：

  N-Aryl Sulfonyl Homocysteine Hydroxamate Inhibitors of Matrix Metalloproteinases:  Further Probing of the S₁, S₁‘, and S₂‘ Pockets

  摘要：

  A series of N-arylsulfonyl S-alkyl homocysteine hydroxamic acids were synthesized with variations in three subsites corresponding to P-1, P-1', and P-2'. Enzyme assays with a variety of MMPs revealed activity at the low nanomolar level.

  DOI：

  10.1021/jm010097f

文献信息

• Picking the S1, S1′ and S2′ pockets of matrix metalloproteinases. A niche for potent acyclic sulfonamide inhibitors
  作者：Stephen Hanessian、Samir Bouzbouz、A Boudon、Gordon C Tucker、Delphine Peyroulan

  DOI：10.1016/s0960-894x(99)00259-0

  日期：1999.6

  A series of acyclic hydroxamic acids harboring strategically placed alpha-arylsulfonamido and thioether groups was synthesized and found to be potent inhibitors of various MMPs. An unprecedented cleavage of t-butyl hydroxamates to hydroxamic acids was found. (C) 1999 Elsevier Science Ltd. All rights reserved.
• US6063816A
  申请人：——

  公开号：US6063816A

  公开（公告）日：2000-05-16
• <i>N</i>-Aryl Sulfonyl Homocysteine Hydroxamate Inhibitors of Matrix Metalloproteinases:  Further Probing of the S₁, S₁‘, and S₂‘ Pockets
  作者：Stephen Hanessian、Nicolas Moitessier、Cécile Gauchet、Martin Viau

  DOI：10.1021/jm010097f

  日期：2001.9.1

  A series of N-arylsulfonyl S-alkyl homocysteine hydroxamic acids were synthesized with variations in three subsites corresponding to P-1, P-1', and P-2'. Enzyme assays with a variety of MMPs revealed activity at the low nanomolar level.