2-[2-[Bis(carboxymethyl)amino]ethyl-[2-[6-[[2-[[2-[6-[[2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetyl]amino]hexanoylamino]thiazole-4-carbonyl]amino]thiazole-4-carbonyl]amino]hexylamino]-2-oxo-ethyl]amino]acetic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[2-[Bis(carboxymethyl)amino]ethyl-[2-[6-[[2-[[2-[6-[[2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetyl]amino]hexanoylamino]thiazole-4-carbonyl]amino]thiazole-4-carbonyl]amino]hexylamino]-2-oxo-ethyl]amino]acetic acid
• 英文别名: 2-[2-[bis(carboxymethyl)amino]ethyl-[2-[6-[[2-[[2-[6-[[2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetyl]amino]hexanoylamino]-1,3-thiazole-4-carbonyl]amino]-1,3-thiazole-4-carbonyl]amino]hexylamino]-2-oxoethyl]amino]acetic acid
• 化学式: C₄₀H₅₉N₁₁O₁₇S₂
• 分子量: 1030.1
• InChiKey: JHSFKFKDDNKHQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.7
• 重原子数：
  70
• 可旋转键数：
  39
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  465
• 氢给体数：
  11
• 氢受体数：
  25

反应信息

• 作为产物：
  描述：

  1-triphenylmethyl-1,6-diaminohexane 在 吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2-[2-[Bis(carboxymethyl)amino]ethyl-[2-[6-[[2-[[2-[6-[[2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetyl]amino]hexanoylamino]thiazole-4-carbonyl]amino]thiazole-4-carbonyl]amino]hexylamino]-2-oxo-ethyl]amino]acetic acid
  参考文献：
  名称：

  Inhibition of HIV-1 integrase-catalysed reaction by new DNA minor groove ligands: the oligo-1,3-thiazolecarboxamide derivatives

  摘要：

  Human immunodeficiency virus type 1 (HIV-1) integrase (IN) is an essential enzyme in the life cycle of the retrovirus, responsible for catalysing the insertion of the viral genome into the host cell chromosome. For this reason it provides an attractive target for antiviral drug design. We synthesized a series of novel thiazole (Tz)-containing oligopeptides (TCOs; oligo-1,3-thiazolecarboxamides), specifically interacting within the minor groove of DNA. The oligocarboxamide derivatives contained 1-4 Tz rings and different N- and C-terminal groups. The effect of these oligocarboxamides on the HIV-1 IN-catalysed reaction was investigated. Some of the compounds were able to inhibit the reaction. The inhibitory effect of the TCOs increased with the number of Tz units. The structure of various additional positively and/or negatively charged groups attached to the N- and C-termini of TCOs had a pronounced effect on their interaction with the DNA substrate complexed to IN. Modified TCOs having a better affinity for this complex should provide a rationale for the design of drugs targeting the integration step. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01181-8

文献信息

• Inhibition of HIV-1 integrase-catalysed reaction by new DNA minor groove ligands: the oligo-1,3-thiazolecarboxamide derivatives
  作者：Vladimir A. Ryabinin、Alexander N. Sinyakov、Vaea Richard de Soultrait、Anne Caumont、Vincent Parissi、Olga D. Zakharova、Elena L. Vasyutina、Ekaterina Yurchenko、Roman Bayandin、Simon Litvak、Laura Tarrago-Litvak、Georgy A. Nevinsky

  DOI：10.1016/s0223-5234(00)01181-8

  日期：2000.11

  Human immunodeficiency virus type 1 (HIV-1) integrase (IN) is an essential enzyme in the life cycle of the retrovirus, responsible for catalysing the insertion of the viral genome into the host cell chromosome. For this reason it provides an attractive target for antiviral drug design. We synthesized a series of novel thiazole (Tz)-containing oligopeptides (TCOs; oligo-1,3-thiazolecarboxamides), specifically interacting within the minor groove of DNA. The oligocarboxamide derivatives contained 1-4 Tz rings and different N- and C-terminal groups. The effect of these oligocarboxamides on the HIV-1 IN-catalysed reaction was investigated. Some of the compounds were able to inhibit the reaction. The inhibitory effect of the TCOs increased with the number of Tz units. The structure of various additional positively and/or negatively charged groups attached to the N- and C-termini of TCOs had a pronounced effect on their interaction with the DNA substrate complexed to IN. Modified TCOs having a better affinity for this complex should provide a rationale for the design of drugs targeting the integration step. (C) 2000 Editions scientifiques et medicales Elsevier SAS.