ethyl 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]benzoate | 138117-79-0

• 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: ethyl 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]benzoate
• 英文别名: 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]benzoic acid,ethyl ester；4-[3-(6-oxo-1,6-dihydropurin-9-yl)propionylamino]benzoic acid ethyl ester；4-[3-(6-Oxo-1,6-dihydropurin-9-yl)propionylamino]benzoic acid ethyl ester；ethyl 4-[3-(6-oxo-1H-purin-9-yl)propanoylamino]benzoate
• CAS: 138117-79-0
• 化学式: C₁₇H₁₇N₅O₄
• 分子量: 355.353
• InChiKey: OWVIKWJNOLWUFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]benzoate 在 水 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 4-[[3-(6-hydro-1-methyl-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]benzoic acid
  参考文献：
  名称：

  A New Method for Synthesis and Angiogenic Evaluation of Leteprinim Potassium and Its Novel Analogs

  摘要：

  We developed a novel pathway for the successful synthesis of leteprinim potassium 1, which is one of the candidate substances for treating Alzheimer's disease, and subsequently synthesized 4 types of corresponding novel derivatives 2-5 that have hypoxanthine or 2-chloro-6-aminopurine as the nucleobase. We then determined the angiogenic activity of these compounds by using human umbilical vein endothelial cells. Compounds 1-4 showed no angiogenic potencies judging from statistical analysis, student's t-test.

  DOI：

  10.3987/com-13-12824
• 作为产物：
  描述：

  3-(6-aminopurine-9-yl)-propionic acid ethyl ester 在 氯化亚砜 、 水 、 溶剂黄146 、 sodium hydroxide 、 sodium nitrite 作用下， 以 乙腈 为溶剂， 反应 33.0h， 生成 ethyl 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]benzoate
  参考文献：
  名称：

  A New Method for Synthesis and Angiogenic Evaluation of Leteprinim Potassium and Its Novel Analogs

  摘要：

  We developed a novel pathway for the successful synthesis of leteprinim potassium 1, which is one of the candidate substances for treating Alzheimer's disease, and subsequently synthesized 4 types of corresponding novel derivatives 2-5 that have hypoxanthine or 2-chloro-6-aminopurine as the nucleobase. We then determined the angiogenic activity of these compounds by using human umbilical vein endothelial cells. Compounds 1-4 showed no angiogenic potencies judging from statistical analysis, student's t-test.

  DOI：

  10.3987/com-13-12824

文献信息

• Synthesis and methods of use of purine analogues and derivatives
  申请人：——

  公开号：US20020156277A1

  公开（公告）日：2002-10-24

  A purine derivative or analogue comprises a 9-atom bicyclic moiety, moiety A, linked through a linker L to a moiety B, where B is a carboxylic acid, a carboxylic acid ester, or a moiety of the structure N(Y 1 )—D, where Y 1 can be one of a variety of substituents, including hydrogen or alkyl, and D is a moiety that enhances the pharmacological effects, promotes absorption or blood-brain barrier penetration of the derivative or analogue. The moiety A has a six-membered ring fused to a five-membered ring. The moiety A can have one, two, or three nitrogen atoms in the five membered ring and has two nitrogen atoms in the six-membered ring. The moiety A can be a purine moiety. The moiety B can be one of a variety of moieties, including moieties having nootropic activity or other biological or physiological activity.

  一种嘌呤衍生物或类似物包括一个由9个原子构成的双环基团A，通过一个连接基团L连接到一个基团B，其中B是一个羧酸、羧酸酯，或者结构为N(Y1)—D的基团，其中Y1可以是多种取代基之一，包括氢或烷基，D是一个增强药理效应、促进衍生物或类似物吸收或穿透血脑屏障的基团。基团A具有一个与一个五元环融合的六元环。基团A在五元环中可以有一个、两个或三个氮原子，并且在六元环中有两个氮原子。基团A可以是一个嘌呤基团。基团B可以是多种基团之一，包括具有智力活性或其他生物学或生理活性的基团。
• 9-substituted hypoxanthine bi-functional compounds and their
  申请人：——

  公开号：US05091432A1

  公开（公告）日：1992-02-25

  Novel bi-functional pharmaceutical compounds, particularly novel 9-substituted hypoxanthines of the general formula: ##STR1## where R is a neurologically active moiety, are described as pharmaceutical agents for treating neuroimmunologic disorders in mammals. Novel methods for the utilization of these compounds are also disclosed. These compounds exhibit uniquely dose-dependent, synergistic biological properties and are particularly useful for treating interrelated physiological systems.

  新型双重功能药物化合物，特别是一般公式为：##STR1## 其中R是一个神经活性基团，被描述为治疗哺乳动物神经免疫疾病的药物。还公开了利用这些化合物的新方法。这些化合物表现出独特的剂量依赖性、协同生物学特性，特别适用于治疗相互关联的生理系统。
• [EN] MULTI-FUNCTIONAL PHARMACEUTICAL COMPOUNDS AND METHODS OF USE
  申请人：GLASKY, Alvin, J.

  公开号：WO1991014434A1

  公开（公告）日：1991-10-03

  (EN) Novel multi-functional pharmaceutical compounds are disclosed incorporating at least two biologically active chemical structural moieties linked by at least one chemical bridging group. The chemical moieties are chosen to exhibit specific biological activity, including immunological activity, neurological activity, cardiovascular activity, and anti-microbial activity. The multi-functional pharmaceutical compounds exhibit uniquely dose-dependent, synergistic biological properties and are particularly useful for treating inter-related physiological systems.(FR) On décrit de nouveaux composés pharmaceutiques à fonctions multiples qui incluent au moins deux moitiés chimiques structurales biologiquement actives et liées par au moins un groupe de liaison pontée chimique. Les moitiés chimiques sont choisies en fonction des activités biologiques spécifiques qu'elles présentent, y compris l'activité immunologique, l'activité neurologique, l'activité cardiovasculaire et l'activité antimicrobienne. Les composés pharmaceutiques à fonctions multiples présentent des propriétés biologiques synergiques dépendant de la manière unique du dosage, et sont particulièrement utiles au traitement de systèmes physiologiques reliés entre eux.

  介绍了一种新型多功能药物化合物，其包含至少两个生物活性化学结构基团，由至少一个化学桥接基团连接。所选择的化学基团具有特定的生物活性，包括免疫活性、神经活性、心血管活性和抗微生物活性。这些多功能药物化合物表现出独特的剂量依赖性、协同作用的生物特性，特别适用于治疗相互关联的生理系统。
• Methods for treatment of disease-induced peripheral neuropathy and related conditions
  申请人：Spectrum Pharmaceuticals, Inc.

  公开号：EP1790344A2

  公开（公告）日：2007-05-30

  The use of a compound of formula (I) in the manufacture of a medicament for the treatment of peripheral neuropathy. The compound can induce peripheral nerve sprouting through the action of a neurotrophic factor such as nerve growth factor (NGF) without the occurrence of hyperalgesia. The peripheral nerve sprouting can be nociceptive nerve sprouting.

  将式（I）化合物用于制造治疗周围神经病变的药物。该化合物可通过神经生长因子（NGF）等神经营养因子的作用诱导周围神经萌发，而不会出现痛觉减退。外周神经萌发可以是痛觉神经萌发。
• Methods for stimulation of synthesis of synaptophysin in the central nervous system
  申请人：——

  公开号：US20020040032A1

  公开（公告）日：2002-04-04

  A method of increasing the synthesis and/or secretion of synaptophysin comprises administering to a patient with a neurological disease or a patient at risk of developing a neurological disease an effective quantity of a purine derivative or analogue, a tetrahydroindolone derivative or analogue, or a pyrimidine derivative or analogue. If the compound is a purine derivative, the purine moiety can be guanine or hypoxanthine. The neurological disease can be a neurodegenerative disease such as Alzheimer's disease or a neurodevelopmental disorder such as Down's syndrome. Typically, the compound can pass through the blood-brain barrier. The purine moiety can be hypoxanthine or guanine. A particularly preferred purine derivative is N-4-carboxyphenyl-3-(6-oxohydropurin-9-yl) propanamide.

  一种增加突触素合成和/或分泌的方法包括向神经系统疾病患者或有患神经系统疾病风险的患者施用有效量的嘌呤衍生物或类似物、四氢吲哚酮衍生物或类似物或嘧啶衍生物或类似物。如果化合物是嘌呤衍生物，嘌呤分子可以是鸟嘌呤或次黄嘌呤。神经系统疾病可以是神经退行性疾病，如阿尔茨海默病，也可以是神经发育障碍，如唐氏综合征。通常情况下，化合物可以通过血脑屏障。嘌呤分子可以是次黄嘌呤或鸟嘌呤。一种特别优选的嘌呤衍生物是 N-4-羧基苯基-3-（6-氧代氢嘌呤-9-基）丙酰胺。