[3-(aminomethyl)phenyl]guanidine | 180079-84-9

• 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: [3-(aminomethyl)phenyl]guanidine
• 英文别名: 2-[3-(Aminomethyl)phenyl]guanidine
• CAS: 180079-84-9
• 化学式: C₈H₁₂N₄
• 分子量: 164.21
• InChiKey: WULVAFIGHJBILA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  90.4
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-[[bis[[(1,1-dimethylethoxy)carbonyl]amino]methylene]amino]benzylamine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以57.7%的产率得到[3-(aminomethyl)phenyl]guanidine
  参考文献：
  名称：

  Specificity of a Prodrug-Activating Enzyme hVACVase: The Leaving Group Effect

  摘要：

  Human valacyclovirase (hVACVase) is a prodrug-activating enzyme for amino acid prodrugs including the antiviral drugs valacyclovir and valganciclovir. In hVACVase-catalyzed reactions, the leaving group of the substrate corresponds to the drug moiety of the prodrug, making the leaving group effect essential for the rational design of new prodrugs targeting hVACVase activation. In this study, a series of valine esters, phenylalanine esters, and a valine amide were characterized for the effect of the leaving group on the efficiency of hVACVase-mediated prodrug activation. Except for phenylalanine methyl and ethyl esters, all of the ester substrates exhibited a relatively high specificity constant (k(cat)/K-m), ranging from 850 to 9490 mM(-1).s(-1). The valine amide Val-3-APG exhibited significantly higher K-m and lower k(cat) values compared to the corresponding ester Val-3-HPG, indicating poor specificity for hVACVase. In conclusion, the substrate leaving group has been shown to affect both binding and specific activity of hVACVase-catalyzed activation. It is proposed that hVACVase is an ideal target for a-amino acid ester prodrugs with relatively labile leaving groups while it is relatively inactivate toward amide prodrugs.

  DOI：

  10.1021/mp100300k

文献信息

• ANILINE DERIVATIVES HAVING NITROGEN MONOXIDE SYNTHASE INHIBITORY ACTIVITY
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0798292B1

  公开（公告）日：2004-11-03
• US9771345B2
  申请人：——

  公开号：US9771345B2

  公开（公告）日：2017-09-26
• Specificity of a Prodrug-Activating Enzyme hVACVase: The Leaving Group Effect
  作者：Jing Sun、Arik Dahan、Zachary F. Walls、Longsheng Lai、Kyung-Dall Lee、Gordon L. Amidon

  DOI：10.1021/mp100300k

  日期：2010.12.6

  Human valacyclovirase (hVACVase) is a prodrug-activating enzyme for amino acid prodrugs including the antiviral drugs valacyclovir and valganciclovir. In hVACVase-catalyzed reactions, the leaving group of the substrate corresponds to the drug moiety of the prodrug, making the leaving group effect essential for the rational design of new prodrugs targeting hVACVase activation. In this study, a series of valine esters, phenylalanine esters, and a valine amide were characterized for the effect of the leaving group on the efficiency of hVACVase-mediated prodrug activation. Except for phenylalanine methyl and ethyl esters, all of the ester substrates exhibited a relatively high specificity constant (k(cat)/K-m), ranging from 850 to 9490 mM(-1).s(-1). The valine amide Val-3-APG exhibited significantly higher K-m and lower k(cat) values compared to the corresponding ester Val-3-HPG, indicating poor specificity for hVACVase. In conclusion, the substrate leaving group has been shown to affect both binding and specific activity of hVACVase-catalyzed activation. It is proposed that hVACVase is an ideal target for a-amino acid ester prodrugs with relatively labile leaving groups while it is relatively inactivate toward amide prodrugs.