(3aS,4R,5S,7R,7aR)-5-(dodecylamino)-7-methylhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexan]-4-ol | 628724-28-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4R,5S,7R,7aR)-5-(dodecylamino)-7-methylhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexan]-4-ol
• CAS: 628724-28-7
• 化学式: C₂₅H₄₇NO₃
• 分子量: 409.653
• InChiKey: PFCNGKGYUWOAEF-HUUMMWPTSA-N

物化性质

• 沸点：
  532.7±50.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.71
• 重原子数：
  29.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.72
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3aS,4R,5S,7R,7aR)-5-(dodecylamino)-7-methylhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexan]-4-ol 在 溶剂黄146 作用下， 以 水 为溶剂， 生成 N-dodecyl-5a-carba-β-DL-fucopyranosylamine
  参考文献：
  名称：

  Synthesis and glycosidase inhibitory activity of some N-substituted 5a-carba-β-fuco- and β-galactopyranosylamines, and selected derivatives

  摘要：

  In the course of chemical modification of alpha-fucosidase inhibitors of 5a-carba-fucopyranosylamine type, an N-dodecyl derivative of the enantiomer 6-deoxy-5a-carba-beta-(D)-galactopyranosylamitie demonstrated very strong inhibition of beta-galactosidase and beta-glucosidase. This finding led us to synthesize corresponding 6-hydroxy compounds, in order to elucidate structure-activity relationships for inhibitors of this type. Among four N-alkyl-5a-carba-beta-(D)-galactopyranosylatnines prepared, the N-octyl derivative could be demonstrated to possess moderate activity toward alpha- and beta-galactosidases, and beta-glucosidase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.023
• 作为产物：
  描述：

  3-O-benzoyl-1,5-anhydro-2,6-dideoxy-4-O-mesyl-5a-carba-DL-arabino-hex-1-enitol 在 disodium hydrogenphosphate 、 disodium hydrogenphosphate 、 sodium methylate 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 263.0h， 生成 (3aS,4R,5S,7R,7aR)-5-(dodecylamino)-7-methylhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexan]-4-ol
  参考文献：
  名称：

  Synthesis and glycosidase inhibitory activity of some N-substituted 5a-carba-β-fuco- and β-galactopyranosylamines, and selected derivatives

  摘要：

  In the course of chemical modification of alpha-fucosidase inhibitors of 5a-carba-fucopyranosylamine type, an N-dodecyl derivative of the enantiomer 6-deoxy-5a-carba-beta-(D)-galactopyranosylamitie demonstrated very strong inhibition of beta-galactosidase and beta-glucosidase. This finding led us to synthesize corresponding 6-hydroxy compounds, in order to elucidate structure-activity relationships for inhibitors of this type. Among four N-alkyl-5a-carba-beta-(D)-galactopyranosylatnines prepared, the N-octyl derivative could be demonstrated to possess moderate activity toward alpha- and beta-galactosidases, and beta-glucosidase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.023

文献信息

• Synthesis and glycosidase inhibitory activity of some N -Substituted 6-Deoxy-5a-carba-β- dl - and l -galactopyranosylamines
  作者：Seiichiro Ogawa、Shigeo Fujieda、Yuko Sakata、Masahiro Ishizaki、Seiichi Hisamatsu、Kensuke Okazaki

  DOI：10.1016/s0960-894x(03)00742-x

  日期：2003.10

  Chemical modification of 5a-carba-beta-DL-fucopyranosylamine (3) generated six N-substituted derivatives 9a-f, among which N-octyl 9b, decyl 9c, and phenylbutyl ones 9f were found to be very strong beta-galactosidase as well as beta-glucosidase inhibitors. The inhibitory activity appeared attributable to D-enantiomers from biological assays of prepared L-enantiomers. Therefore, 6-deoxy-5a-carba-beta-D-galactopyranosylamine (D-3) might be a promising lead compound for further design of new carba sugar-type P-galactosidase inhibitors. (C) 2003 Elsevier Ltd. All rights reserved.