isopropyl 6-O-acetyl-3-[hydroxy-(4-nitrophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranos-4-uloside | 819803-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: isopropyl 6-O-acetyl-3-[hydroxy-(4-nitrophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranos-4-uloside
• 英文别名: [(2S,6R)-4-[(R)-hydroxy-(4-nitrophenyl)methyl]-5-oxo-2-propan-2-yloxy-2H-pyran-6-yl]methyl acetate
• CAS: 819803-40-2
• 化学式: C₁₈H₂₁NO₈
• 分子量: 379.367
• InChiKey: ISZXRHNHDLZVIA-IXDOHACOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  isopropyl 6-O-acetyl-3-[hydroxy-(4-nitrophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranos-4-uloside 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 乙醇 为溶剂， 以73%的产率得到isopropyl-6-O-acetyl-3-[hydroxy-(4-nitrophenyl)methyl]-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  C-3 Alkyl/Arylalkyl-2,3-dideoxy Hex-2-enopyranosides as Antitubercular Agents:  Synthesis, Biological Evaluation, and QSAR Study

  摘要：

  A series of C-3 alkyl and arylalkyl 2,3-dideoxy hex-2-enopyranoside derivatives were synthesized by Morita-Baylis-Hillman reaction using enulosides 4,5, and 6 and various aliphatic and aromatic aldehydes. The compounds were evaluated in vitro for the complete inhibition of growth of Mycobacterium tuberculosis H37Rv. They exhibited moderate to good activity in the range of 25-1.56 mu g/mL. Among these, 4d, 4h, 5c, and 4hr showed activity at minimum inhibitory concentrations, 3.12, 6.25, 1.56, and 1.56 mu g/mL, respectively. These compounds were safe against cytotoxicity in VERO cell line and mouse macrophage cell line J 744A.1. A QSAR analysis by CP-MLR with alignment-free 3D-descriptors indicated the relevance of structure space comparable to the minimum energy conformation (from conformational analysis) of 5c to the activity. The study indicates that the compounds attaining the conformational space of 5c and reflecting some symmetry, minimum eccentricity, and closely placed geometric and electronegativity centers therein are favorable for activity.

  DOI：

  10.1021/jm070110h
• 作为产物：
  描述：

  isopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 吡啶 、 manganese(IV) oxide 、 sodium methylate 、 四氯化钛 、 四丁基碘化铵 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 50.0h， 生成 isopropyl 6-O-acetyl-3-[hydroxy-(4-nitrophenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranos-4-uloside
  参考文献：
  名称：

  C-3 Alkyl/Arylalkyl-2,3-dideoxy Hex-2-enopyranosides as Antitubercular Agents:  Synthesis, Biological Evaluation, and QSAR Study

  摘要：

  A series of C-3 alkyl and arylalkyl 2,3-dideoxy hex-2-enopyranoside derivatives were synthesized by Morita-Baylis-Hillman reaction using enulosides 4,5, and 6 and various aliphatic and aromatic aldehydes. The compounds were evaluated in vitro for the complete inhibition of growth of Mycobacterium tuberculosis H37Rv. They exhibited moderate to good activity in the range of 25-1.56 mu g/mL. Among these, 4d, 4h, 5c, and 4hr showed activity at minimum inhibitory concentrations, 3.12, 6.25, 1.56, and 1.56 mu g/mL, respectively. These compounds were safe against cytotoxicity in VERO cell line and mouse macrophage cell line J 744A.1. A QSAR analysis by CP-MLR with alignment-free 3D-descriptors indicated the relevance of structure space comparable to the minimum energy conformation (from conformational analysis) of 5c to the activity. The study indicates that the compounds attaining the conformational space of 5c and reflecting some symmetry, minimum eccentricity, and closely placed geometric and electronegativity centers therein are favorable for activity.

  DOI：

  10.1021/jm070110h

文献信息

• Regioselective synthesis of densely functionalized, enantiopure, sugar–pyrazole hybrids as potential scaffolds for drug discovery
  作者：Mohammad Saquib、Irfan Husain、Ruchir Kant、Sanjeev Meena、H. M. Gauniyal、Sudhir Sinha、P. R. Maulik、Arun K. Shaw

  DOI：10.1039/c3ra22287j

  日期：——

  A versatile new synthetic strategy utilizing MBH chemistry for the assembly of highly functionalized enantiopure sugar–pyrazole hybrid molecules with multiple sites for structural diversification and a non-flat skeleton as potential drug scaffolds is reported. Four representative hybrid molecules were screened for in vitro anti-cancer activity, wherein three of them were found to exhibit good anti-cancer activity.

  报道了一种利用MBH化学的新型多功能合成策略，用于组装具有多个结构多样化位点和非平面骨架的高度官能化手性纯糖-吡唑杂化分子，这些分子可作为潜在药物骨架。通过筛选四种代表性杂化分子在体外抗肿瘤活性，发现其中三种表现出良好的抗肿瘤活性。
• A substrate controlled, very highly diastereoselective Morita–Baylis–Hillman reaction: a remote activation of the diastereofacial selectivity in the synthesis of C-3-branched deoxysugars
  作者：Ram Sagar、Chandra Shekhar Pant、Rashmi Pathak、Arun K. Shaw

  DOI：10.1016/j.tet.2004.09.086

  日期：2004.12

  The Morita-Baylis-Hillman (MBH) reaction of p-nitrobenzaldehyde with C (6) acyl protected enuloside 1 in the presence of TiCl4/TBAI yielded highly diastereoenriched C-3-branched deoxysugar derivative or MBH adduct 1'a in high yield, while reactions of unprotected enuloside 2a and C (6) alkyl protected enulosides 2d-e with p-nitrobenzaldehyde under the same conditions afforded the adducts 2'a and 2'd-e, respectively, in low yield with moderate selectivity. Several representative aromatic and aliphatic aldehydes were selected to undergo MBH reaction with I to give their respective adducts in very good yield with a very high diastereoselectivity. A plausible mechanism based on the assumption of a Zimmerman-Traxler-type transition state was proposed to explain the excellent selectivity observed with adducts derived from 1. The synthetic application of these adducts were shown by their stereoselective reduction to corresponding threo isomers in very good yield. (C) 2004 Elsevier Ltd. All rights reserved.