tert-butyl (3aR,4R,6aR)-4-(hydroxymethyl)-2,2-dimethyl-6-oxotetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate | 1107649-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (3aR,4R,6aR)-4-(hydroxymethyl)-2,2-dimethyl-6-oxotetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• 英文别名: N-tert-butoxycarbonyl-4-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactam
• CAS: 1107649-78-4
• 化学式: C₁₃H₂₁NO₆
• 分子量: 287.313
• InChiKey: QGIHOXQNFUQKMZ-IWSPIJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  85.3
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (3aR,4R,6aR)-4-(hydroxymethyl)-2,2-dimethyl-6-oxotetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Functionalized pyrrolidine inhibitors of human type II α-mannosidases as anti-cancer agents: Optimizing the fit to the active site

  摘要：

  Refining the chemical structure of functionalized pyrrolidine-based inhibitors of Golgi alpha-mannosidase II (GMII) to optimize binding affinity provided a lead molecule that demonstrated nanomolar competitive inhibition of alpha-mannosidases II and an optimal fit in the active site of Drosophila GMII by X-ray crystallography. Esters of this lead compound also inhibited the growth of human glioblastoma and brain-derived endothelial cells more than the growth of non-tumoral human fibroblasts, suggesting their potential for anti-cancer therapy.

  DOI：

  10.1016/j.bmc.2008.06.021
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 sodium periodate 、 silica gel 、 对甲苯磺酸 、 柠檬酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 9.33h， 生成 tert-butyl (3aR,4R,6aR)-4-(hydroxymethyl)-2,2-dimethyl-6-oxotetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
  参考文献：
  名称：

  Total synthesis of both enantiomers of trans-2,3-cis-3,4-dihydroxyproline

  摘要：

  Both enantiomers of trans-2,3-cis-3,4-dihydroxyproline, 4 and 5, have been stereoselectively synthesized from 2,3-O-isopropylidene-D-glyceraldehyde 1, by taking advantage of a divergent and parallel synthetic strategy, utilizing N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as the common four-carbon synthon. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00123-1

文献信息

• Inhibition of LuxS by S-ribosylhomocysteine analogues containing a [4-aza]ribose ring
  作者：Venkata L.A. Malladi、Adam J. Sobczak、Tiffany M. Meyer、Dehua Pei、Stanislaw F. Wnuk

  DOI：10.1016/j.bmc.2011.07.043

  日期：2011.9

  LuxS (S-ribosylhomocysteinase) catalyzes the cleavage of the thioether linkage of S-ribosylhomocysteine (SRH) to produce homocysteine and 4,5-dihydroxy-2,3-pentanedione (DPD), the precursor to a small signaling molecule that mediates interspecies bacterial communication called autoinducer 2 (AI-2). Inhibitors of LuxS should interfere with bacterial interspecies communication and potentially provide a novel class of antibacterial agents. In this work, SRH analogues containing substitution of a nitrogen atom for the endocyclic oxygen as well as various deoxyriboses were synthesized and evaluated for LuxS inhibition. Two of the [4-aza] SRH analogues showed modest competitive inhibition (K-I similar to 40 mu M), while most of the others were inactive. One compound that contains a hemiaminal moiety exhibited time-dependent inhibition, consistent with enzyme-catalyzed ring opening and conversion into a more potent species (K-I* = 3.5 mu M). The structure-activity relationship of the designed inhibitors highlights the importance of both the homocysteine and ribose moieties for high-affinity binding to LuxS active site. (C) 2011 Elsevier Ltd. All rights reserved.