isopropyl-6-O-4-nitrobenzoyl-3-[hydroxy-(4-trifluoromethylphenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranoside-4-ulose | 945030-51-3

• 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-4-nitrobenzoyl-3-[hydroxy-(4-trifluoromethylphenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranoside-4-ulose
• 英文别名: [(2S,6R)-4-[(R)-hydroxy-[4-(trifluoromethyl)phenyl]methyl]-5-oxo-2-propan-2-yloxy-2H-pyran-6-yl]methyl 4-nitrobenzoate
• CAS: 945030-51-3
• 化学式: C₂₄H₂₂F₃NO₈
• 分子量: 509.436
• InChiKey: VDJVVKQGSQALIR-QHAWAJNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  isopropyl-6-O-4-nitrobenzoyl-3-[hydroxy-(4-trifluoromethylphenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranoside-4-ulose 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 乙醇 为溶剂， 以80%的产率得到isopropyl-6-O-4-nitrobenzoyl-3-[hydroxy-(4-trifluoromethylphenyl)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-4-nitrobenzoyl-3-[hydroxy-(4-trifluoromethylphenyl)methyl]-2,3-dideoxy-α-D-glycero-hex-2-enopyranoside-4-ulose
  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

• C-3 Alkyl/Arylalkyl-2,3-dideoxy Hex-2-enopyranosides as Antitubercular Agents:  Synthesis, Biological Evaluation, and QSAR Study
  作者：Mohammad Saquib、Manish K. Gupta、Ram Sagar、Yenamandra S. Prabhakar、Arun K. Shaw、Rishi Kumar、Prakas R. Maulik、Anil N. Gaikwad、Sudhir Sinha、Anil K. Srivastava、Vinita Chaturvedi、Ranjana Srivastava、Brahm S. Srivastava

  DOI：10.1021/jm070110h

  日期：2007.6.1

  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.