O-guanidino-L-homoserine methyl ester

• 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: O-guanidino-L-homoserine methyl ester
• 英文别名: O-Guanidino-L-homoserin-methylester; (S)-O-(3-Amino-3-carbomethoxy-propyl)-N-guanyl-hydroxylamin；(S)-O-(3-Amino-3-carbomethoxy-propyl)-N-guanyl-hydroxylamin；O-Guanidino-L-homoserin-methylester；L-Canavanin-methylester；methyl (2S)-2-amino-4-(diaminomethylideneamino)oxybutanoate
• 化学式: C₆H₁₄N₄O₃
• 分子量: 190.202
• InChiKey: LTYQWEVXKPLDNG-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O-guanidino-L-homoserine methyl ester 、 (S)-2-(1-((tert-butoxycarbonyl)amino)-3-methylbutyl)oxazole-4-carboxylic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  [EN] MODULATORS OF C3A RECEPTORS
  [FR] MODULATEURS DES RÉCEPTEURS C3A

  摘要：

  描述了调节C3a受体的杂环化合物及其在治疗或预防炎症性疾病、传染病、癌症、代谢紊乱、肥胖、2型糖尿病、代谢综合征以及相关心血管疾病中的用途。还描述了这些化合物在刺激或抑制免疫反应中的用途，以及包含这些化合物或其药用可接受盐的制药组合物。

  公开号：

  WO2013067578A1
• 作为产物：
  描述：

  甲醇 、 L-刀豆氨酸 在 盐酸 作用下， 反应 1.0h， 以71%的产率得到O-guanidino-L-homoserine methyl ester
  参考文献：
  名称：

  Insecticidal properties of some derivatives of L-canavanine

  摘要：

  The canavanine derivatives D-canavanine and L-homocanavanine as well as the 1-methyl and 1-ethyl esters of L-canavanine were synthesized and evaluated for biological activity in fifth instar larvae of the tobacco hornworm, Manduca sexta [Sphingidae]. While L-homocanavanine did not increase intrinsic toxicity, it was as deleterious as L-canavanine. D-Canavanine was biologically active, as demonstrated by its ability to cause larval edema, but the D-enantiomer had little ability to elicit the larval growth inhibition and pupal deformity which are hallmarks of canavanine toxicosis and was postulated to be linked to aberrant protein production. The 1-methyl and 1-ethyl esters of L-canavanine were synthesized to determine if enhancing canavanine's hydrophobicity might increase its bioavailability. Our experiments revealed that these esters are less toxic than canavanine; the ethyl ester disrupted larval growth more than did the methyl analogue.

  DOI：

  10.1021/jf00058a034

文献信息

• [EN] STRUCTURE OF PLASMEPSIN V IN COMPLEX WITH AN INHIBITOR AND USES THEREOF<br/>[FR] STRUCTURE DE PLASMEPSINE V ASSOCIÉE AU SEIN D'UN COMPLEXE AVEC UN INHIBITEUR, ET UTILISATION CORRESPONDANTE
  申请人：THE WALTER AND ELIZA HALL INST OF MEDICAL RES

  公开号：WO2016197190A1

  公开（公告）日：2016-12-15

  In one aspect, the present invention relates to the crystal structure of Plasmodium vivax plasmepsin V in complex with an inhibitor, and to methods of using the crystal structure and related structural information to identify, design and/or screen for inhibitors or redesign known inhibitors that interact with and/or modulate plasmepsin V activity. In another aspect, the present invention relates to a class of compounds based on the inhibitor useful in the treatment of malaria.

  在一个方面，本发明涉及与抑制剂结合的疟原虫间日疟原虫质膜蛋白酶V的晶体结构，以及利用晶体结构和相关的结构信息来鉴定、设计和/或筛选与/或调节质膜蛋白酶V活性相互作用的抑制剂或重新设计已知的抑制剂的方法。在另一个方面，本发明涉及一类基于该抑制剂的化合物，可用于治疗疟疾。