isopropyl 6-O-acetyl-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose | 819803-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: isopropyl 6-O-acetyl-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose
• 英文别名: [(2S,6R)-2-isopropoxy-5-oxo-2H-pyran-6-yl]methyl acetate；[(2S,6R)-5-oxo-2-propan-2-yloxy-2H-pyran-6-yl]methyl acetate
• CAS: 819803-37-7
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: PPFPEVPUWVHUGF-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  isopropyl 6-O-acetyl-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose 在 sodium tetrahydroborate 、 cerium(III) chloride 、 四氯化钛 、 四丁基碘化铵 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 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 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 50.0h， 生成 isopropyl 6-O-acetyl-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-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

• Facile Synthesis of Enantiomerically Pure 2- and 2,3-Disubstituted Furans Catalysed by Mixed Lewis Acids: An Easy Route to 3-Iodofurans and 3-(Hydroxymethyl)furans
  作者：Mohammad Saquib、Irfan Husain、Brijesh Kumar、Arun K. Shaw

  DOI：10.1002/chem.200900007

  日期：2009.6.8

  Enantiopure furan synthesis: A synthesis, catalysed by mixed Lewis acids (ZrCl4/ZnI2), of enantiomerically pure 2‐ and 2,3‐disubstituted furan derivatives, including 3‐iodofuran and 3‐ (hydroxymethyl)furan derivatives, in good to very good yields from commercially available 3,4,6‐tri‐O‐acetyl‐D‐glucal is described. Key features of this method are the use of inexpensive reagents in catalytic amounts

  对映纯呋喃合成：由混合路易斯酸（ZrCl 4 / ZnI 2）催化的对映体纯的2和2,3-二取代呋喃衍生物，包括3-碘呋喃和3-（羟甲基）呋喃衍生物描述了从商业上可获得的3,4,6- tri - O-乙酰基-D-葡萄糖的非常好的收率。该方法的主要特点是使用廉价的催化量试剂，温和的反应条件和简便的后处理程序。
• 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.
• 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.
• 2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies
  作者：Mohammad Saquib、Irfan Husain、Smriti Sharma、Garima Yadav、Vipul K. Singh、Sandeep K. Sharma、Priyanka Shah、Mohammad Imran Siddiqi、Brijesh Kumar、Jawahar Lal、Girish K. Jain、Brahm S. Srivastava、Ranjana Srivastava、Arun K. Shaw

  DOI：10.1016/j.ejmech.2011.03.002

  日期：2011.6

  The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents. These easily accessible, small molecules were found to exhibit in vitro activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.78 mu g/mL to 25 mu g/mL. A detailed SAR study on these hex-2-enopyranosid-4-uloses led to the identification of compound 5g (5007-724) which on the basis of low MIC (0.78 mu g/mL-M. tuberculosis H37Rv; 1.56 mu g/mL-MDR, SDR strains of M. tuberculosis; 0.78 mu g/mL-inhibition of intracellular replication of M. tuberculosis) and SI value of 13.5 has been identified as a promising lead molecule. (C) 2011 Elsevier Masson SAS. All rights reserved.