3-(6-amino-purin-9-yl)-propionic acid methyl ester | 70259-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 3-(6-amino-purin-9-yl)-propionic acid methyl ester
• 英文别名: 3-(6-aminopurin-9-yl)propionic acid methyl ester；9-(carbomethoxyethyl)adenine；methyl 3-(adenin-9-yl)propionate；3-(Adenin-9-yl)-propionic acid methyl ester；Methyl 3-(6-amino-9h-purin-9-yl)propanoate；methyl 3-(6-aminopurin-9-yl)propanoate
• CAS: 70259-15-3
• 化学式: C₉H₁₁N₅O₂
• 分子量: 221.219
• InChiKey: WEKDUZGYGCHJTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  182-183 °C
• 沸点：
  455.2±55.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(6-amino-purin-9-yl)-propionic acid methyl ester 在 盐酸 、 水 作用下， 反应 3.0h， 以95%的产率得到6-氨基-9H-嘌呤-9-丙酸
  参考文献：
  名称：

  Synthesis and biological evaluation of immunosuppressive agent DZ2002 and its stereoisomers

  摘要：

  DZ2002 and its related stereoisomers were efficiently synthesized. The optical data of (R)- and (S)-DZ2002 were disclosed here for the first time. Their inhibitory potency was evaluated on SAHase and MLR assay in the mean time. In accordance with respective inhibitory potency of SAHase, the immunosuppressive potency order was demonstrated as (S)-Z2002 > (Rac)-DZ2002 > (R)-DZ2002 > (Keto)DZ2002. These results indicate (S)-configuration of 2-chiral center in DZ2002 is important for binding with SAHase. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.017
• 作为产物：
  描述：

  3-溴丙酸甲酯 、 腺嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-(6-amino-purin-9-yl)-propionic acid methyl ester
  参考文献：
  名称：

  基于异羟肟酸酯的腺苷酸环化酶抑制剂。第1部分：无环接头对P位点结合的影响。

  摘要：

  腺苷酸环化酶（AC）是一类酶，由于其将ATP转化为cAMP的能力而成为信号转导的关键元素。这种转化的催化机制是通过ATP与嘌呤结合位点（P-位点）的初始结合而进行的，随后是金属介导的环化反应而失去了焦磷酸盐。用已知抑制剂对AC进行的晶体学分析表明，活性位点中存在两种金属。目前，已知腺苷酸环化酶的九种同工型，并且以组织特异性的方式表达独特的同工型组合。腺苷酸环化酶同工型特异性抑制剂的开发可能被证明是设计新型治疗剂的有用策略。为了开发新型AC抑制剂，我们选择了一种利用腺嘌呤环系统分子通过柔性无环接头与金属配位异羟肟酸连接的设计方法。对设计的抑制剂针对V AC型进行分析，其中接头的大小和杂原子含量发生变化，以探测酶中核苷酸和金属结合位点的相互作用。

  DOI：

  10.1016/s0960-894x(02)00653-4

文献信息

• Reversible inhibitors of SAH hydrolase and uses thereof
  申请人：——

  公开号：US20040204429A1

  公开（公告）日：2004-10-14

  The present invention provides compositions and methods for reversibly inhibiting S-adenosyl-L-homocysteine (SAH) hydrolase. The compounds of the present invention can be used in combination with an anti-hemorrhagic viral infection agent, an immunosuppressant, a homocysteine lowering agent, or an anti-neoplasm agent. The compositions and methods of the present invention can be used for the prevention and treatment of hemorrhagic virus infection, autoimmune diseases, autograft rejection, neoplasm, hyperhomocysteineuria, cardiovascular disease, stroke, Alzheimer's disease, or diabetes.

  本发明提供了用于可逆地抑制S-腺苷基-L-同型半胱氨酸（SAH）水解酶的组合物和方法。本发明的化合物可与抗出血性病毒感染药物、免疫抑制剂、降低同型半胱氨酸的药物或抗肿瘤剂结合使用。本发明的组合物和方法可用于预防和治疗出血性病毒感染、自身免疫疾病、自体移植排斥、肿瘤、高同型半胱氨酸尿症、心血管疾病、中风、阿尔茨海默病或糖尿病。
• Adenine based inhibitors of adenylyl cyclase, pharmaceutical compositions, and method of use thereof
  申请人：——

  公开号：US20020068745A1

  公开（公告）日：2002-06-06

  The present invention relates to derivatives and analogues of adenine, which inhibit adenylyl cyclase activity. The present invention also relates to a method of preventing and inhibiting a patient's fibroproliferative vasculopathy following vascular injury or a vascular surgical operation which includes administering to the patient, an effective amount of a compound according to the invention subsequent to a vascular injury, or subsequent to a vascular surgical operation, for one to two weeks after the injury or surgical operation, effective to treat or prevent a patient's fibroproliferative vasculopathy such as chronic allograft rejection or vascular restenosis following vascular trauma. The present invention also relates to a method for measuring the inhibition of adenylyl cyclase activity and a method for treating congestive heart failure.

  本发明涉及腺嘌呤的衍生物和类似物，其抑制腺苷酸环化酶活性。本发明还涉及一种预防和抑制患者血管损伤后纤维增殖性血管病的方法，或血管手术后的方法，包括向患者施用根据本发明的化合物的有效量，即在血管损伤后或血管手术后的一到两周内，有效地治疗或预防患者的纤维增殖性血管病，如慢性移植物排斥或血管创伤后的血管再狭窄。本发明还涉及一种测量腺苷酸环化酶活性抑制的方法和一种治疗充血性心力衰竭的方法。
• Promiscuous enzyme-catalyzed regioselective Michael addition of purine derivatives to α,β-unsaturated carbonyl compounds in organic solvent
  作者：Jun-Liang Wang、Jian-Ming Xu、Qi Wu、De-Shui Lv、Xian-Fu Lin

  DOI：10.1016/j.tet.2009.01.056

  日期：2009.3

  Michael addition of purine derivatives to α,β-unsaturated carbonyl compounds could be catalyzed by d-aminoacylase amano (DA) in DMSO. The influence of reaction conditions on the Michael addition, including solvent, temperature, and enzyme concentration was systematically investigated. Then we extended this methodology to six structurally diverse purine derivatives and a variety of α,β-unsaturated carbonyl

  嘌呤衍生物向α，β-不饱和羰基化合物的区域选择性迈克尔加成反应可通过DMSO中的d-氨酰基酶天冬氨酸（DA）催化。系统地研究了反应条件对迈克尔加成反应的影响，包括溶剂，温度和酶浓度。然后，我们将此方法扩展到六个结构上不同的嘌呤衍生物和各种α，β-不饱和羰基化合物。以中等至高收率选择性合成了21种迈克尔加合物。这是关于酶催化的迈克尔加成反应制备嘌呤衍生物的第一份报道。
• Reversible inhibitors of S-adenosyl-L-homocysteine hydrolase and uses thereof
  申请人：Yuan Chong-Sheng

  公开号：US20050182075A1

  公开（公告）日：2005-08-18

  The present invention provides compositions and methods for reversibly inhibiting S-adenosyl-L-homocysteine (SAH) hydrolase. The compounds of the present invention can be used in combination with an anti-hemorrhagic viral infection agent, an immunosuppressant, a homocysteine lowering agent, or an anti-neoplasm agent. The compositions and methods of the present invention can be used for the prevention and treatment of hemorrhagic virus infection, autoimmune diseases, autograft rejection, neoplasm, hyperhomocysteineuria, cardiovascular disease, stroke, Alzheimer's disease, or diabetes.

  本发明提供了可逆抑制S-腺苷基-L-同型半胱氨酸（SAH）水解酶的组合物和方法。本发明的化合物可以与抗出血性病毒感染药物、免疫抑制剂、降低同型半胱氨酸的药物或抗肿瘤药物结合使用。本发明的组合物和方法可用于预防和治疗出血性病毒感染、自身免疫性疾病、自体移植排斥、肿瘤、高同型半胱氨酸血症、心血管疾病、中风、阿尔茨海默病或糖尿病。
• Brahme, Nanda M.; Smith, Walter T., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 109 - 112
  作者：Brahme, Nanda M.、Smith, Walter T.

  DOI：——

  日期：——