methyl (S)-4-oxo-1-(phenylsulfonyl)pyrrolidine-2-carboxylate | 20275-04-1

• 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: methyl (S)-4-oxo-1-(phenylsulfonyl)pyrrolidine-2-carboxylate
• 英文别名: 4-Oxo-N-benzolsulfonyl-prolinmethylester；1-Benzenesulfonyl-4-oxo-pyrrolidine-2-carboxylicacid methyl ester；methyl (2S)-1-(benzenesulfonyl)-4-oxopyrrolidine-2-carboxylate
• CAS: 20275-04-1
• 化学式: C₁₂H₁₃NO₅S
• 分子量: 283.305
• InChiKey: LDLLYKAZPLGUFZ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (S)-4-oxo-1-(phenylsulfonyl)pyrrolidine-2-carboxylate 、 1,3-丙二醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以51%的产率得到methyl (3S)-2-(benzenesulfonyl)-6,10-dioxa-2-azaspiro[4.5]decane-3-carboxylate
  参考文献：
  名称：

  Design, synthesis and evaluation of novel sulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors

  摘要：

  A series of novel sulfonyl pyrrolidine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and aminopeptidase N (AP-N). The results showed that these pyrrolidine derivatives exhibited highly selective inhibition against MMP-2 as compared with AP-N. Compounds 6a-d were more potent MMP-2 inhibitors than the positive control LY52. The structure-activity relationships were also briefly discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.027
• 作为产物：
  描述：

  methyl (2S,4S)-4-hydroxy-1-(phenylsulfonyl)pyrrolidine-2-carboxylate 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以88%的产率得到methyl (S)-4-oxo-1-(phenylsulfonyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Design, synthesis and binding properties of a fluorescent α₉β₁/α₄β₁integrin antagonist and its application as anin vivoprobe for bone marrow haemopoietic stem cells

  摘要：

  一种具有纳摇结合亲和力的荧光α9β1整合素拮抗剂已被证明能够结合骨髓造血干细胞和祖细胞体内。

  DOI：

  10.1039/c3ob42332h

文献信息

• Design, synthesis and binding properties of a fluorescent α₉β₁/α₄β₁integrin antagonist and its application as an<i>in vivo</i>probe for bone marrow haemopoietic stem cells
  作者：Benjamin Cao、Oliver E. Hutt、Zhen Zhang、Songhui Li、Shen Y. Heazlewood、Brenda Williams、Jessica A. Smith、David N. Haylock、G. Paul Savage、Susan K. Nilsson

  DOI：10.1039/c3ob42332h

  日期：——

  A fluorescent α₉β₁integrin antagonist with nanomolar binding affinities has been demonstrated to bind bone marrow haemopoietic stem and progenitor cellsin vivo.

  一种具有纳摇结合亲和力的荧光α9β1整合素拮抗剂已被证明能够结合骨髓造血干细胞和祖细胞体内。
• Design, synthesis and evaluation of novel sulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors
  作者：Xian-Chao Cheng、Qiang Wang、Hao Fang、Wei Tang、Wen-Fang Xu

  DOI：10.1016/j.bmc.2008.04.027

  日期：2008.5

  A series of novel sulfonyl pyrrolidine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and aminopeptidase N (AP-N). The results showed that these pyrrolidine derivatives exhibited highly selective inhibition against MMP-2 as compared with AP-N. Compounds 6a-d were more potent MMP-2 inhibitors than the positive control LY52. The structure-activity relationships were also briefly discussed. (C) 2008 Elsevier Ltd. All rights reserved.