1,2-O-cyclohexylidene 1D-(1,2,3,4/5)-4-acetamido-5-(methylthio)-1,2,3-cyclopentanetriol | 171032-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1,2-O-cyclohexylidene 1D-(1,2,3,4/5)-4-acetamido-5-(methylthio)-1,2,3-cyclopentanetriol
• 英文别名: N-[(3aR,4R,5S,6R,6aR)-6-hydroxy-4-methylsulfanylspiro[4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole-2,1'-cyclohexane]-5-yl]acetamide
• CAS: 171032-10-3
• 化学式: C₁₄H₂₃NO₄S
• 分子量: 301.407
• InChiKey: NNRRZFPANIXJQI-ZOLYEBIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-O-cyclohexylidene 1D-(1,2,3,4/5)-4-acetamido-5-(methylthio)-1,2,3-cyclopentanetriol 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 吡啶 、 甲醇 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 20.0h， 生成 Acetic acid (1R,2R,3S,4S)-3-acetylamino-4-hydroxy-2-methylsulfanyl-cyclopentyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of α-mannosidase inhibitory activity of three deoxy derivatives of mannostatin A

  摘要：

  Three deoxy derivatives of alpha-mannosidase inhibitor mannostatin A have been synthesized and their inhibitory activity for Jack beans alpha-mannosidase evaluated in order to elucidate roles of each hydroxyl groups of the inhibitor. The 1- and 2-deoxy derivatives have preserved inhibitory potentials although they lowered the activity one-hundred fold compared to the parent, but the 3-deoxy derivative lost activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00224-3
• 作为产物：
  描述：

  [(3aR,4R,5S,6R,6aR)-5-acetamido-4-acetylsulfanylspiro[4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole-2,1'-cyclohexane]-6-yl] (2R)-2-acetyloxy-2-phenylacetate 、 碘甲烷 在 sodium methylate 作用下， 生成 1,2-O-cyclohexylidene 1D-(1,2,3,4/5)-4-acetamido-5-(methylthio)-1,2,3-cyclopentanetriol
  参考文献：
  名称：

  Ogawa, Seiichiro; Kimura, Hiroshi; Uchida, Chikara, Journal of the Chemical Society. Perkin transactions I, 1995, # 13, p. 1695 - 1706

  摘要：

  DOI：

文献信息

• Synthesis and α-Mannosidase Inhibitory Activity of Three Deoxy Derivatives of Mannostatin A
  作者：Seiichiro Ogawa、Takayuki Morikawa

  DOI：10.1002/(sici)1099-0690(200005)2000:9<1759::aid-ejoc1759>3.0.co;2-j

  日期：2000.5

  Three deoxy derivatives 2-4 of the alpha-mannosidase inhibitor mannostatin A (1) were synthesized, and their inhibition of Jack bean alpha-mannosidase was evaluated in order to elucidate the roles of each of the three hydroxyl groups of the inhibitor. The 1- and 2-deoxy derivatives 2 and 3 retained some inhibitory activity, although reduced by a factor of about 100 relative to the parent, whereas it was completely lost with the 3-deoxy derivative 4. Structure and activity relationships are discussed in the light of these findings.