methyl 3-amino-4-cyano-1-methyl-5-phenyl-1H-pyrrole-2-carboxylate | 587868-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 3-amino-4-cyano-1-methyl-5-phenyl-1H-pyrrole-2-carboxylate
• 英文别名: methyl 3-amino-4-cyano-1-methyl-5-phenylpyrrole-2-carboxylate
• CAS: 587868-34-6
• 化学式: C₁₄H₁₃N₃O₂
• 分子量: 255.276
• InChiKey: RZDVYEJFLHCQCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  81
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-amino-4-cyano-1-methyl-5-phenyl-1H-pyrrole-2-carboxylate 在 三氯氧磷 作用下， 反应 74.0h， 生成 5-methyl-4-oxo-6-phenyl-4-thioxo-3-hydropyrrolo[3,2-d]pyrimidine-7-carbonitrile
  参考文献：
  名称：

  EP1477489

  摘要：

  公开号：
• 作为产物：
  描述：

  1,1-二氰基-2-甲氧基-2-(苯基)乙烯 在 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 4.17h， 生成 methyl 3-amino-4-cyano-1-methyl-5-phenyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  EP1477489

  摘要：

  公开号：

文献信息

• Synthesis, antibacterial, and antifungal activities of new pyrimidinone derivatives
  作者：Oussama Cherif、Fatma Masmoudi、Fatma Allouche、Fakher Chabchoub、Mohamed Trigui

  DOI：10.1515/hc-2015-0066

  日期：2015.8.1

  An efficient synthesis of new pyrrolopyrimidinones 3a-d and isoxazolopyrimidinones 4a-c from the respective aminocyanopyrroles 1a-d and aminocyanoisoxazoles 2a-c is presented. The synthesized compounds were screened for antimicrobial activity against a panel of bacteria and fungi. Compound 4c exhibits remarkable activity against a broad spectrum of Gram-positive and Gram-negative bacteria and pathogenic fungi.

  摘要：本文介绍了从相应的氨基氰基吡咯并吡啶酮3a-d和氨基氰基异噁唑并吡啶酮4a-c高效合成的方法。合成的化合物被筛选用于抗菌活性测试，对一系列细菌和真菌显示出活性。化合物4c对广谱的革兰氏阳性和阴性细菌以及病原真菌表现出显著活性。
• Synthesis and fluorescence properties of aminocyanopyrrole and aminocyanothiophene esthers for biomedical and bioimaging applications
  作者：Oussama Cherif、Asma Agrebi、Sérgio Alves、Carlos Baleizão、José Paulo Farinha、Fatma Allouche

  DOI：10.1016/j.molstruc.2020.127974

  日期：2020.6

  Abstract We prepared a series of substituted aminocyanopyrroles and another of aminocynaothiophenes. We describe an efficient new one-step synthetic strategy via the condensation of an alkyl sarcosinate and ethoxymethylenemalononitrile, through a Gewald-like reaction. The UV–visible absorption and steady-state and time resolved fluorescence properties of some representative compounds, as well as their

  摘要 我们制备了一系列取代氨基氰基吡咯和另一种氨基氰基噻吩。我们描述了一种有效的新一步合成策略，通过类似 Gewald 的反应，使烷基肌氨酸盐和乙氧基亚甲基丙二腈缩合。还介绍了一些代表性化合物的紫外可见吸收和稳态和时间分辨荧光特性，以及它们的酸碱行为。这些化合物可能可用于医学应用和生物成像探针。
• Pyrrolopyrimidine derivatives
  申请人：Kataoka Kenichiro

  公开号：US20050277773A1

  公开（公告）日：2005-12-15

  The invention provides pyrrolo[3,2-d]pyrimidine derivatives represented by formula (I), and their medically acceptable salts. The compounds of the invention exhibit GSK-3 inhibiting activity and are therefore expected to be useful as therapeutic or prophylactic agents for conditions in which GSK-3 is implicated, such as diabetes, diabetes complications, Alzheimer's disease, neurodegenerative diseases, manic depression, traumatic encephalopathy, alopecia, inflammatory diseases, cancer and immune deficiency.

  本发明提供了由式(I)表示的吡咯并[3,2-d]嘧啶衍生物及其医学上可接受的盐。本发明的化合物表现出GSK-3抑制活性，因此预计可用作治疗或预防与GSK-3有关的疾病的治疗或预防剂，例如糖尿病、糖尿病并发症、阿尔茨海默病、神经退行性疾病、躁郁症、创伤性脑病、脱发、炎症性疾病、癌症和免疫缺陷。
• Substituted pyrrolo[3,2-d]pyrimidines as glycogen synthase kinase (GSK) inhibitors
  申请人：Teijin Limited

  公开号：US07528140B2

  公开（公告）日：2009-05-05

  The invention provides pyrrolo[3,2-d]pyrimidine derivatives represented by formula (I), and their medically acceptable salts. The compounds of the invention exhibit GSK-3 inhibiting activity and are therefore expected to be useful as therapeutic or prophylactic agents for conditions in which GSK-3 is implicated, such as diabetes, diabetes complications, Alzheimer's disease, neurodegenerative diseases, manic depression, traumatic encephalopathy, alopecia, inflammatory diseases, cancer and immune deficiency.

  本发明提供了由式(I)表示的吡咯并[3,2-d]嘧啶衍生物及其医学上可接受的盐。本发明的化合物表现出GSK-3抑制活性，因此预计可用作治疗或预防GSK-3涉及的疾病的治疗或预防剂，如糖尿病、糖尿病并发症、阿尔茨海默病、神经退行性疾病、躁狂抑郁症、创伤性脑病、脱发、炎症性疾病、癌症和免疫缺陷。
• PYRROLOPYRIMIDINE DERIVATIVES
  申请人：TEIJIN LIMITED

  公开号：EP1477489A1

  公开（公告）日：2004-11-17

  The invention provides pyrrolo[3,2-d]pyrimidine derivatives represented by formula (I), and their medically acceptable salts. The compounds of the invention exhibit GSK-3 inhibiting activity and are therefore expected to be useful as therapeutic or prophylactic agents for conditions in which GSK-3 is implicated, such as diabetes, diabetes complications, Alzheimer's disease, neurodegenerative diseases, manic depression, traumatic encephalopathy, alopecia, inflammatory diseases, cancer and immune deficiency.

  本发明提供了由式（I）代表的吡咯并[3,2-d]嘧啶衍生物及其医学上可接受的盐类。本发明的化合物具有 GSK-3 抑制活性，因此有望作为治疗或预防药物，用于治疗与 GSK-3 有关的疾病，如糖尿病、糖尿病并发症、阿尔茨海默病、神经退行性疾病、躁狂抑郁症、创伤性脑病、脱发、炎症性疾病、癌症和免疫缺陷。