(3R,4R)-trans-N-Boc-3-acetoxy-4-azidopyrrolidine | 1214272-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R,4R)-trans-N-Boc-3-acetoxy-4-azidopyrrolidine
• 英文别名: (3R,4R)-N-Boc-3-azido-4-acetoxypyrrolidine；tert-butyl (3R,4R)-3-acetyloxy-4-azidopyrrolidine-1-carboxylate
• CAS: 1214272-51-1
• 化学式: C₁₁H₁₈N₄O₄
• 分子量: 270.288
• InChiKey: QFFSENIVSIMCJV-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4R)-trans-N-Boc-3-acetoxy-4-azidopyrrolidine 在 甲醇 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,4R)-tert-butyl 3-azido-4-hydroxypyrrolidine-1-carboxylate
  参考文献：
  名称：

  Substituted Heterocyclic Mercaptosulfonamide Metalloprotease Inhibitors

  摘要：

  本发明一般涉及取代的杂环巯基磺酰胺化合物、前体及其衍生物，以及制备这些化合物的方法和包含这些化合物的药物组合物。这些化合物被设计为强效的选择性基质金属蛋白酶（MMPs）抑制剂，包括例如明胶酶、胶原酶、基质溶素、金属弹性蛋白酶、基质溶素和膜型1基质金属蛋白酶。这些抑制剂可用于控制生理和病理过程以及疾病状况，在这些过程中，MMPs被认为发挥着重要作用。

  公开号：

  US20110144179A1
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium azide 、 乙酸异丙烯酯 、 lipase Amano AK-20 、 氯化铵 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 甲基叔丁基醚 、 水 为溶剂， 反应 72.0h， 生成 (3R,4R)-trans-N-Boc-3-acetoxy-4-azidopyrrolidine
  参考文献：
  名称：

  Matrix Metalloproteinase Inhibitors Based on the 3-Mercaptopyrrolidine Core

  摘要：

  New series of pyrrolidine mercaptosulfide, 2-mercaptocyclopentane arylsulfonamide, and 3-mercapto-4-arylsulfonamidopyrrolidine matrix metalloproteinase inhibitors (MMPIs) were designed, synthesized, and evaluated. Exhibiting unique properties over other MMPIs (e.g., hydroxamates), these newly reported compounds are capable of modulating activities of several MMPs in the low nanomolar range, including MMP-2 (similar to 2 to 50 nM), MMP-13 (similar to 2 to 50 nM), and MMP-14 (similar to 4 to 60 nM). Additionally these compounds are selective to intermediate- and deep-pocket MMPs but not shallow-pocketed MMPs (e.g., MMP-1, similar to 850 to >50 000 nM; MMP-7, similar to 4000 to >25 000 nM). Our previous work with the mercaptosulfide functionality attached to both cyclopentane and pyrrolidine frameworks demonstrated that the cis-(3S,4R)-stereochemistry was optimal for all of the MMPs tested. However, in our newest compounds an interesting shift of preference to the trans form of the mercaptosulfonamides was observed with increased oxidative stability and biological compatibility. We also report several kinetic and biological characteristics showing that these compounds may be used to probe the mechanistic activities of MMPs in disease.

  DOI：

  10.1021/jm400529f

文献信息

• Substituted heterocyclic mercaptosulfonamide metalloprotease inhibitors
  申请人：Schwartz Martin A.

  公开号：US08404866B2

  公开（公告）日：2013-03-26

  The present invention generally relates to substituted heterocyclic mercaptosulfonamide compounds, precursors, and derivatives as well as methods for the preparation of and pharmaceutical compositions comprising these compounds. These compounds are designed to be potent selective inhibitors of matrix metalloproteinases (MMPs), including, for example, gelatinases, collagenases, matrilysins, metalloelastase, stromelysin, and membrane-type 1 matrix metalloproteinase. These inhibitors may be used for the control of physiological and pathological processes and disease conditions in which MMPs are believed to play significant functions.

  本发明涉及取代杂环巯基磺酰胺化合物、前体和衍生物以及制备这些化合物和制药组合物的方法。这些化合物被设计为针对基质金属蛋白酶（MMPs）的强效选择性抑制剂，包括明胶酶、胶原酶、基质蛋白酶、金属弹性蛋白酶、基质金属蛋白酶1型等。这些抑制剂可用于控制生理和病理过程以及疾病状态，其中MMPs被认为发挥重要作用。
• US8404866B2
  申请人：——

  公开号：US8404866B2

  公开（公告）日：2013-03-26
• [EN] SUBSTITUTED HETEROCYCLIC MERCAPTOSULFONAMIDE METALLOPROTEASE INHIBITORS<br/>[FR] INHIBITEURS MERCAPTOSULFONAMIDES HÉTÉROCYCLIQUES SUBSTITUÉS DE MÉTALLOPROTÉINASE
  申请人：UNIV FLORIDA STATE RES FOUND

  公开号：WO2010028051A2

  公开（公告）日：2010-03-11

  The present invention generally relates to substituted heterocyclic mercaptosulfonamide compounds, precursors, and derivatives as well as methods for the preparation of and pharmaceutical compositions comprising these compounds. These compounds are designed to be potent selective inhibitors of matrix metalloproteinases (MMPs), including, for example, gelatinases, collagenases, matrilysins, metalloelastase, stromelysin, and membrane-type 1 matrix metalloproteinase. These inhibitors may be used for the control of physiological and pathological processes and disease conditions in which MMPs are believed to play significant functions.