(+)-proto-quercitol | 1157852-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-proto-quercitol
• 英文别名: 1,2:3,4-di-O-isopropylidene-5R-(+)-proto-quercitol；(1S,2S,6S,7R,9R)-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-ol
• CAS: 1157852-09-9
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: DMHGPKRSZAXQJK-ZJDVBMNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-proto-quercitol 在 四氧化锇 、 三氟甲磺酸酐 、 N-甲基吗啉氧化物 作用下， 以 吡啶 、 甲醇 、 水 、 叔丁醇 为溶剂， 反应 27.0h， 生成 epi-Inositol
  参考文献：
  名称：

  从天然存在的（+）-原-槲皮醇中合成（+）-硬脑膜糖醇F和肌醇类似物及其葡糖苷酶抑制活性

  摘要：

  描述了由天然可得的（+）-原-槲皮醇有效合成（+）-硬脂醇F，（+）-手性-和（+）-表肌醇。这种合成方法提供了对映体纯净形式的环糖醇的简明合成。在合成的环糖醇中，（+）-conduritol F有效抑制I型α-葡萄糖苷酶，IC 50值为86.1μM ，是标准抗糖尿病药物阿卡波糖的五倍。

  DOI：

  10.1016/j.bmcl.2012.01.007
• 作为产物：
  描述：

  原栎醇 以75的产率得到(+)-proto-quercitol
  参考文献：
  名称：

  Bioorg. Med. Chem. Lett. 2012, 22, 1538-1540

  摘要：

  DOI：

文献信息

• Voglibose-inspired synthesis of new potent α-glucosidase inhibitors N-1,3-dihydroxypropylaminocyclitols
  作者：Wisuttaya Worawalai、Pornthep Sompornpisut、Sumrit Wacharasindhu、Preecha Phuwapraisirisan

  DOI：10.1016/j.carres.2016.04.014

  日期：2016.6

  (+)-proto-quercitol (1) as a cyclitol core structure. The newly synthesized compounds revealed potent rat intestinal α-glucosidases, particularly against maltase, with IC50 values at submicromolar. Subsequent study on mechanisms underlying the inhibition of 11 indicated the competitive manner towards maltase and sucrase. The potent inhibition of these compounds was elaborated by docking study, in which their binding

  伏格列波糖（一种N-1,3-二羟丙基氨基环糖醇）已广泛用作糖尿病治疗的有效α-葡萄糖苷酶抑制剂。已经进行了多种尝试，以通过各种氨基环糖醇和丙烷-1，3-二醇的偶联来合成紧密相关的类似物。然而，它们大多数显示出较弱的抑制作用或没有抑制作用。在这次交流中，我们使用（+）-原-槲皮醇（1）作为环糖醇核心结构合成了一对新的N-1,3-二羟丙基氨基环糖醇（10和11）。新合成的化合物显示出强效的大鼠肠道α-葡萄糖苷酶，尤其是针对麦芽糖酶的酶，其IC50值为亚微摩尔。随后对11抑制作用机理的研究表明了对麦芽糖酶和蔗糖酶的竞争方式。通过对接研究详细阐述了这些化合物的有效抑制作用，其中它们与活性位点中关键氨基酸残基的结合曲线与伏格列波糖相似。因此，将丙烷-1,3-二醇部分引入合适的环己烷核心结构（如氨基槲皮醇）将是发现一系列新的有效α-葡萄糖苷酶抑制剂的潜在途径。
• (+)-proto-Quercitol, a natural versatile chiral building block for the synthesis of the α-glucosidase inhibitors, 5-amino-1,2,3,4-cyclohexanetetrols
  作者：Sumrit Wacharasindhu、Wisuttaya Worawalai、Wimolpun Rungprom、Preecha Phuwapraisirisan

  DOI：10.1016/j.tetlet.2009.02.153

  日期：2009.5

  diastereomerically pure 5-amino-1,2,3,4-cyclohexanetetrols (6 and 11) and quercitol derivatives from naturally available (+)-proto-quercitol (1) is described. The stereochemistry of 1 is perfectly set up for regioselective protection of the hydroxy group which was further functionalized into the target aminocyclitol in a straightforward manner. The present approach provides a protocol for preparing aminocyclitols

  描述了由天然可得的（+）-原-槲皮醇（1）有效合成非对映体纯的5-氨基-1,2,3,4-环己烷四醇（6和11）和槲皮醇衍生物。立体化学1的建立是为了对羟基进行区域选择性保护，该羟基以直接的方式进一步官能化成目标氨基环糖醇。本方法提供了用于大量制备氨基环醇的方案。另外，使用改进的Mosher方法解决了（+）-原-槲皮醇的绝对立体化学。在合成的氨基环糖醇中，有11种可能通过IC抑制α-葡萄糖苷酶50值12.5μM，其比标准降糖药，阿卡波糖的大45倍的®。
• Potent chemical chaperone compounds for G_M1-gangliosidosis: N-substituted (+)-conduramine F-4 derivatives
  作者：Shinichi Kuno、Katsumi Higaki、Atsushi Takahashi、Eiji Nanba、Seiichiro Ogawa

  DOI：10.1039/c4md00270a

  日期：——

  The development of chemical chaperones to decrease the inhibitory activity while increasing the enzyme enhancement activity is described.

  描述了开发化学伴侣来降低抑制活性并增加酶增强活性的过程。
• Transformation of quercitols into 4-methylenecyclohex-5-ene-1,2,3-triol derivatives, precursors for the chemical chaperones N-octyl-4-epi-β-valienamine (NOEV) and N-octyl-β-valienamine (NOV)
  作者：Shinichi Kuno、Atsushi Takahashi、Seiichiro Ogawa

  DOI：10.1016/j.bmcl.2011.09.067

  日期：2011.12

  (+)-proto-Quercitol (1) and (-)-vibo-quercitol (2), both of which could be readily prepared by the bioconversion of myo-inositol, were successfully converted into the corresponding 4-methylenecyclohex-5-ene-1,2,3-triol derivatives. These compounds were demonstrated to be suitable precursors, preserving their configurations, for bioactive carba-aminosugars such as the potent chemical chaperone drug candidates, N-octyl-4-epi-beta-valienamine (NOEV, 3) and N-octyl-beta-valienamine (NOV, 4). (C) 2011 Elsevier Ltd. All rights reserved.

  (+)-原儿茶糖苷醇(1)和(-)-威博儿茶糖苷醇(2)，这两种糖苷均可以通过肌醇的生物转化简便制备，成功转化为了相应的4-甲基环己-5-烯-1,2,3-三醇衍生物。研究证明，这些化合物在保留其构型的情况下，适合作为具有生物活性的氨基糖（如强效化学伴侣药物候选物N-辛基-4-表-β-戊吡胺醇(3)和N-辛基-β-戊吡胺醇(4)）的前体。 (以上译文仅供参考，英文原文版权为2011 Elsevier Ltd.所有，保留所有权利。)
• Quercitylcinnamates, a new series of antidiabetic bioconjugates possessing α-glucosidase inhibition and antioxidant
  作者：Eakkaphon Rattanangkool、Preecha Kittikhunnatham、Thanakorn Damsud、Sumrit Wacharasindhu、Preecha Phuwapraisirisan

  DOI：10.1016/j.ejmech.2013.05.047

  日期：2013.8

  Antidiabetic agents possessing dual functions, alpha-glucosidase inhibition and antioxidant, have been accepted to be more useful than currently used antidiabetic drugs because they not only suppress hyperglycemia but also prevent risk of complications. Herein, we design antidiabetic bioconjugates comprising of (+)-proto-quercitol as a glucomimic and cinnamic analogs as antioxidant moieties. Fifteen quercitylcinnamates were synthesized by direct coupling through ester bond in the presence of DCC and DMAP. Particular quercityl esters 6a, 7a and 8a selectively inhibited rat intestinal maltase and sucrose 4 -6 times more potently than their parents 6, 7 and 8. Of synthesized bioconjugates, 6a was the most potent inhibitor against maltase and sucrose with IC50 values of 531 and 43.65 mu M, respectively. Of interest, its inhibitory potency toward maltase was 6 times greater than its parent, caffeic acid (6), while its radical scavenging (SC50 0.11 mM) was comparable to that of commercial antioxidant BHA. Subsequent investigation on mechanism underlying inhibitory effect of 6a indicated that it blocked maltase and sucrose functions by mixed inhibition through competitive and noncompetitive manners. (C) 2013 Elsevier Masson SAS. All rights reserved.