(S)-N-(2-(theophylline-7-yl)acetyl)valine methyl ester | 1612254-04-2

• 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: (S)-N-(2-(theophylline-7-yl)acetyl)valine methyl ester
• 英文别名: methyl (2S)-2-[[2-(1,3-dimethyl-2,6-dioxo-purin-7-yl)acetyl]amino]-3-methyl-butanoate；methyl (2S)-2-[[2-(1,3-dimethyl-2,6-dioxopurin-7-yl)acetyl]amino]-3-methylbutanoate
• CAS: 1612254-04-2
• 化学式: C₁₅H₂₁N₅O₅
• 分子量: 351.362
• InChiKey: ZBTLOQZUZJDVRN-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-N-(2-(theophylline-7-yl)acetyl)valine methyl ester 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以90%的产率得到(S)-N-(2-(theophylline-7-yl)acetyl)valine
  参考文献：
  名称：

  Theophylline-7-acetic acid derivatives with amino acids as anti-tuberculosis agents

  摘要：

  A series of amides were synthesized by condensation of theophylline-7-acetic acid and eight commercially available amino acid methyl ester hydrochlorides. Consecutive hydrolysis of six of the amido-esters resulted in the formation of corresponding amido-acids. The newly synthesized compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv. The activity varied depending on the amino acid fragments and in seven cases exerted excellent values with MICs 0.46-0.26 mu M. Assessment of the cytotoxicity revealed that the compounds were not cytotoxic against the human embryonal kidney cell line HEK-293T. The theophylline-7-acetamides containing amino acid moieties appear to be promising lead compounds for the development of antimycobacterial agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.026
• 作为产物：
  描述：

  茶碱乙酸 、 L-缬氨酸甲酯盐酸盐 在 N,N-二异丙基乙胺 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.17h， 以96%的产率得到(S)-N-(2-(theophylline-7-yl)acetyl)valine methyl ester
  参考文献：
  名称：

  Theophylline-7-acetic acid derivatives with amino acids as anti-tuberculosis agents

  摘要：

  A series of amides were synthesized by condensation of theophylline-7-acetic acid and eight commercially available amino acid methyl ester hydrochlorides. Consecutive hydrolysis of six of the amido-esters resulted in the formation of corresponding amido-acids. The newly synthesized compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv. The activity varied depending on the amino acid fragments and in seven cases exerted excellent values with MICs 0.46-0.26 mu M. Assessment of the cytotoxicity revealed that the compounds were not cytotoxic against the human embryonal kidney cell line HEK-293T. The theophylline-7-acetamides containing amino acid moieties appear to be promising lead compounds for the development of antimycobacterial agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.026

文献信息

• Theophylline-7-acetic acid derivatives with amino acids as anti-tuberculosis agents
  作者：Yulian Voynikov、Violeta Valcheva、Georgi Momekov、Plamen Peikov、Georgi Stavrakov

  DOI：10.1016/j.bmcl.2014.05.026

  日期：2014.7

  A series of amides were synthesized by condensation of theophylline-7-acetic acid and eight commercially available amino acid methyl ester hydrochlorides. Consecutive hydrolysis of six of the amido-esters resulted in the formation of corresponding amido-acids. The newly synthesized compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv. The activity varied depending on the amino acid fragments and in seven cases exerted excellent values with MICs 0.46-0.26 mu M. Assessment of the cytotoxicity revealed that the compounds were not cytotoxic against the human embryonal kidney cell line HEK-293T. The theophylline-7-acetamides containing amino acid moieties appear to be promising lead compounds for the development of antimycobacterial agents. (C) 2014 Elsevier Ltd. All rights reserved.