(1R,2R)-trans-2-azidocyclopentyl acetate | 260065-68-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (1R,2R)-trans-2-azidocyclopentyl acetate
• 英文别名: [(1R,2R)-2-azidocyclopentyl] acetate
• CAS: 260065-68-7
• 化学式: C₇H₁₁N₃O₂
• 分子量: 169.183
• InChiKey: GFVZBYQQTGIDPH-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R)-trans-2-azidocyclopentyl acetate 在 甲醇 、 三苯基膦 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 9.0h， 生成 [(1R,2R)-2-羟基环戊基]氨基甲酸叔丁酯
  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
• 作为产物：
  描述：

  (±)-trans-2-azidocyclopentanol 在 乙酸异丙烯酯 、 lipase Amano AK-20 作用下， 以 甲基叔丁基醚 为溶剂， 反应 72.0h， 以49%的产率得到(1S,2S)-trans-2-azidocyclopentanol
  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

• Lipase-catalyzed Kinetic Resolution of (±)-<i>trans</i>- and<i>cis</i>-2-Azidocycloalkanols
  作者：Ei’ich AMI、Hiroshi OHRUI

  DOI：10.1271/bbb.63.2150

  日期：1999.1

  The lipase-catalyzed kinetic resolution of trans- and cis-2-azidocycloalkanols and the preparation of enantiomerically pure trans- and cis-2-aminocycloalkanols are described. Four kinds of lipases were screened for the acetylation of trans- and cis-2-azidocycloalkanols. Among them, Pseudomonas sp. lipases (lipase PS and lipase AK, Amamo Pharmaceutical Co.) showed the highest enantioselectivity. These

  描述了脂肪酶催化的反式和顺式-2-叠氮基环烷醇的动力学拆分以及对映体纯的反式和顺式-2-氨基环烷醇的制备。筛选了四种脂肪酶，用于反式和顺式-2-叠氮基环烷醇的乙酰化。其中，假单胞菌属sp。脂肪酶（脂肪酶PS和脂肪酶AK，Amomo Pharmaceutical Co.）显示出最高的对映选择性。使用（S）-TBMB羧酸[（S）-2-叔丁基-2-甲基- 1,3-苯并二恶唑-4-羧酸]作为手性转化试剂。CD分析的结果证明N，O-双-（S）-TBMB羧化的顺-2-氨基环烷醇主要采用N-赤道构象。