(+/-)-(1RS,2SR,3SR,4RS)-4-aminocyclohex-5-ene-1,2,3-triol | 79435-30-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-(1RS,2SR,3SR,4RS)-4-aminocyclohex-5-ene-1,2,3-triol
• 英文别名: (1RS,2RS,3SR,6SR)-6-aminocyclohex-4-ene-1,2,3-triol；(+/-)-conduramine B-1；rac-conduramine B1；(+/-)-(1RS,2RS,3SR,6SR)-6-aminocyclohex-4-ene-1,2,3-triol；rac-conduramine B-1；(1R,2R,3S,6S)-6-aminocyclohex-4-ene-1,2,3-triol
• CAS: 79435-30-6；89615-00-9；138513-21-0；139626-79-2；139626-80-5；141269-14-9；142796-97-2；142797-00-0
• 化学式: C₆H₁₁NO₃
• 分子量: 145.158
• InChiKey: RAJLHDDMNNFKNT-UNTFVMJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-(1RS,2SR,3SR,4RS)-4-aminocyclohex-5-ene-1,2,3-triol 在 三乙酰氧基硼氢化钠 作用下， 以 甲醇 为溶剂， 生成 (+/-)-(1RS,2SR,3SR,4RS)-4-{{4-[4-(1,1-dimethoxyethyl)phenoxy]benzyl}amino}cyclohex-5-ene-1,2,3-triol
  参考文献：
  名称：

  （1 S，2 S，3 R，6 R）-6-氨基环己-4-烯-1,2,3-三醇（=（-）-Conduramine B-1）是α-甘露糖苷酶的选择性抑制剂。N-苄基化增强其抑制活性

  摘要：

  （-）-和（+）-Conduramine B-1（（-）-和（+）- 5，分别）衍生自（+）-和（-）-7-氧杂双环[2.2.1]庚烷-5-en-2-one（第一代“裸糖”）。尽管（-）- 5模仿β-葡糖苷的结构，但是它不抑制β-葡糖苷酶，而是选择性地抑制α-甘露糖苷酶。（-）- 5的N-苄基化提高了conduramine B-1作为α-甘露糖苷酶抑制剂的效力，并且还生成了抑制β-葡萄糖苷酶的化合物。例如，（-）- N-苄基-conduramine B-1（（-）- 19a）是β的竞争性抑制剂-来自杏仁（IC 50  = 32μM，K i  = 10μM）的葡萄糖苷酶和来自杰克豆（IC 50  = 171μM）和来自杏仁（IC 50  = 225μM）的α-甘露糖苷酶的弱抑制剂，而（-）- N-（4-苯基苄基）conduramine B-1（（-）- 19g）是来自千斤顶豆的α-甘露糖苷酶的良好抑制剂（IC

  DOI：

  10.1002/hlca.200590220
• 作为产物：
  描述：

  (+/-)-(1,3,4/2)- and (+/-)-(1,3/2,4)-1,2,3-Tri-O-acetyl-4-bromo-5-cyclohexene-1,2,3-triol 在 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 (+/-)-(1RS,2SR,3SR,4RS)-4-aminocyclohex-5-ene-1,2,3-triol
  参考文献：
  名称：

  (±)-6-Acetamido-1,2-anhydro-6-deoxy-myo-inositol: a tight-binding inhibitor and pseudosubstrate for N-acetyl-β-glucosaminidases

  摘要：

  A five-step procedure is described for the synthesis of the title compound (N-acetylconduramine B trans-epoxide, 14) from tetra-O-acetylconduritol B [(+/-)-(1,3/2,4)-1,2,3,4-tetra-0-acetyl-5-cyclohexene-1,2,3,4-tetrol]. Inhibition studies with N-acetyl-beta-glucosaminidases from bovine kidney, jack beans, and Helix pomatia gave K(i) values for 14 of 0.50-1.6 muM, i.e., 500-8000-fold lower than the K(i) for 2-acetamido-2-deoxy-D-glucose. The K(i) values for N-acetylconduramine B [(+/-)-(1,3/2,4)-4-acetamido-5-cyclohexene-1,2,3-triol] and its cis-epoxide [(+/-)-1-acetamido-2,3-anhydro-2-deoxy-myo-inositol] were several orders of magnitude larger than for 14. In contrast to the interaction of other glycosidases with anhydro-inositols of appropriate configuration, there was no covalent, irreversible inhibition. Instead, the first two enzymes catalysed a transformation of 14 into a compound (presumably the oxazoline) which underwent spontaneous hydrolysis at pH less-than-or-equal-to 5. No inhibition was observed with the N-acetyl-beta-glucosaminidase from Aspergillus niger.

  DOI：

  10.1016/s0008-6215(00)90924-8

文献信息

• Total asymmetric synthesis of (−)-conduramine B-1 and of its enantiomer. N-Benzyl derivatives of conduramine B-1 are β-glucosidase inhibitors
  作者：Robert Łysek、Catherine Schütz、Pierre Vogel

  DOI：10.1016/j.bmcl.2005.04.023

  日期：2005.6

  The 'naked sugars' (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one have been converted into (-)-conduramine B-1 ((-)-3) and its enantiomer (+)-3, respectively. They have been condensed with a variety of aldehydes in the presence of NaBH(OAc)(3). The N-substituted derivatives 4 and ent-4 so-obtained have been tested against two alpha-glucosidases, two amyloglucosidases, two beta-glucosidases and one

  “裸糖”（+）-和（-）-7-氧杂双环[2.2.1]庚-5-烯-2-酮已转化为（-）-conduramine B-1（（-）-3）及其对映体（+）-3。在NaBH（OAc）（3）存在下，它们已与多种醛缩合。已经测试了如此获得的N-取代的衍生物4和ent-4针对两种α-葡糖苷酶，两种淀粉葡糖苷酶，两种β-葡糖苷酶和一种β-木糖苷酶的抑制活性。尽管（-）-3和（+）-3在1mM浓度下均不抑制任何这些酶，但（-）-conduramine B-1的N-苄基衍生物是具有K（i）的β-葡萄糖苷酶的选择性和竞争性抑制剂。在低分子范围内。
• Conduramine F-1 epoxides: synthesis and their glycosidase inhibitory activities
  作者：Robert Łysek、Sylvain Favre、Pierre Vogel

  DOI：10.1016/j.tet.2007.03.149

  日期：2007.7

  Starting from (+/-)-7-oxanorbornenone ((+/-)-14), (+/-)-(1RS, 2RS, 3SR, 6SR)-6-azidocyclohex-4-en-1,2,3-triol ((+/-)-24) and (+/-)- 1RS, 2RS, 3SR, 6RS)-6-azidocyclohex-4-en-1,2,3-triol ((+/-)-26) were obtained. Epoxidation of the latter cyclohexene derivative gave two epoxides (+/-)-30 and (+/-)-31 that were converted into (+/-)-conduramine F-1 epoxides (+/-)-10 and (epoxides (+/-)-30 and (+/-)-31 that were converted into (+/-)-conduramine F-1 epoxides (+/-)-10 and (+/-)-11 and N-substituted derivatives (+/-)-12 and (+/-)-13. Compound (+/-)-(1RS, 2SR, 3RS, 4SR, 5RS, 6SR)-5-([4-(trifluoromethyl) phenyl] methyl} amino)-7-oxabicyclo[4.1.0]heptane-2,3,4- triol ((+/-)-12c) is a good, non-competitive inhibitor of beta-xylosidase from Aspergillus niger (K-i=2.2 mu M), and (+/-)( 1RS, 2RS, 3SR, 4RS, 5SR, 6SR)-5-[(biphenyl-4-yl) methyl] amino}-7-oxabicyclo[4.1.0] heptane-2,3,4-triol ((+/-)-13d) is a good inhibitor of alpha-glucosidase from brewer's yeast (Ki 2.8 mu M, non-competitive). (c) 2007 Elsevier Ltd. All rights reserved.