2-Pyridin-3-yl-3,5-dihydro-pyrimido[5,4-b]indol-4-one | 158183-93-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-Pyridin-3-yl-3,5-dihydro-pyrimido[5,4-b]indol-4-one
• 英文别名: 2-(3-Pyridyl)-3,5-dihydropyrimido[5,4-b]indol-4-one；2-pyridin-3-yl-3,5-dihydropyrimido[5,4-b]indol-4-one
• CAS: 158183-93-8
• 化学式: C₁₅H₁₀N₄O
• 分子量: 262.271
• InChiKey: QQCGGTRCPUDAPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Pyridin-3-yl-3,5-dihydro-pyrimido[5,4-b]indol-4-one 在 三氯氧磷 作用下， 反应 10.0h， 以16%的产率得到4-Chloro-2-pyridin-3-yl-5H-pyrimido[5,4-b]indole
  参考文献：
  名称：

  Synthesis and anti-HIV-1 activities of new pyrimido[5,4-b]indoles

  摘要：

  A set of new pyrimido[5,4-b]indole derivatives that are structurally related to some non-nucleoside HIV-I reverse transcriptase inhibitors were synthesized and biologically evaluated for their activity as inhibitors of wild and mutant HIV-1 RT types in an 'in vitro' recombinant HIV-1 RT screening assay, as well as anti-infectives in HLT4lacZ-1(IIIB) cells. Preliminary structure-activity relationships suggest that activity is promoted by simultaneous substitution in positions 2 and 4, especially when chains of alkyldiamine type are present, and by electron-releasing substituents (methoxy) in positions 7 and 8. The inactivity or the very low activity of title derivatives does not suggest interest in AIDS therapy. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00035-x
• 作为产物：
  描述：

  3-氰基吡啶 、 3-氨基-2-吲哚羧酸乙酯 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以18%的产率得到2-Pyridin-3-yl-3,5-dihydro-pyrimido[5,4-b]indol-4-one
  参考文献：
  名称：

  Synthesis and anti-HIV-1 activities of new pyrimido[5,4-b]indoles

  摘要：

  A set of new pyrimido[5,4-b]indole derivatives that are structurally related to some non-nucleoside HIV-I reverse transcriptase inhibitors were synthesized and biologically evaluated for their activity as inhibitors of wild and mutant HIV-1 RT types in an 'in vitro' recombinant HIV-1 RT screening assay, as well as anti-infectives in HLT4lacZ-1(IIIB) cells. Preliminary structure-activity relationships suggest that activity is promoted by simultaneous substitution in positions 2 and 4, especially when chains of alkyldiamine type are present, and by electron-releasing substituents (methoxy) in positions 7 and 8. The inactivity or the very low activity of title derivatives does not suggest interest in AIDS therapy. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00035-x

文献信息

• US5326868A
  申请人：——

  公开号：US5326868A

  公开（公告）日：1994-07-05
• US5463054A
  申请人：——

  公开号：US5463054A

  公开（公告）日：1995-10-31
• [EN] CERTAIN ARYL FUSED PYRROLOPYRIMIDINES; A NEW CLASS OF GABA BRAIN RECEPTOR LIGANDS<br/>[FR] PYRROLAPYRIMIDINES CONDENSEES PAR UN ARYLE CONSTITUANT UNE NOUVELLE CATEGORIE DE LIGANDS DES RECEPTEURS CEREBRAUX DU GABA
  申请人：NEUROGEN CORPORATION

  公开号：WO1994025463A1

  公开（公告）日：1994-11-10

  (EN) The present invention encompasses structures of formula (I) and the pharmaceutically acceptable non-toxic salts thereof wherein: (1) represents (2), (3), (4) or (5) and X represents hydrogen, halogen, or hydroxy; W represents an aryl group unsubstituted or substituted with various organic and inorganic substituents; A, B, C, D and E represent carbon or nitrogen substituted with hydrogen or various organic and inorganic substituents; and R3 and R4 are variables representing various organic and inorganic substituents. These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs thereof and are useful in the diagnosis and treatment of anxiety, sleep and seizure disorders, overdose with benzodiazepine drugs and enhancement of memory.(FR) Structures de la formule (I) et leurs sels pharmacompatibles non toxiques oú (1) représente (2), (3), (4) ou (5) et X représente un hydrogène, un halogène ou un hydroxy; W représente un groupe aryle non substitué ou substitué par différents substituants organiques ou inorganiques; A, B, C, D et E représentent un carbone ou un azote substitué par un hydrogène ou différents substituants; R3 et R4 sont des variables représentant différents substituants organiques ou inorganiques. Ces composés sont des agonistes, des antagonistes ou des agonistes inverses à haute sélectivité des récepteurs cérébraux du GABAa et de leurs prodrogues. Ils sont utiles dans le diagnostique et le traitement de troubles liés à l'anxiété, au sommeil et aux crises cérébrales, et de surdoses de benzodiazépine, ainsi que pour accroître la vivacité.
• Synthesis and anti-HIV-1 activities of new pyrimido[5,4-b]indoles
  作者：Isidro Merino、Antonio Monge、Marı́a Font、Juan José Martı́nez de Irujo、Elena Alberdi、Esteban Santiago、Isidro Prieto、Juan José Lasarte、Pablo Sarobe、Francisco Borrás

  DOI：10.1016/s0014-827x(99)00035-x

  日期：1999.4

  A set of new pyrimido[5,4-b]indole derivatives that are structurally related to some non-nucleoside HIV-I reverse transcriptase inhibitors were synthesized and biologically evaluated for their activity as inhibitors of wild and mutant HIV-1 RT types in an 'in vitro' recombinant HIV-1 RT screening assay, as well as anti-infectives in HLT4lacZ-1(IIIB) cells. Preliminary structure-activity relationships suggest that activity is promoted by simultaneous substitution in positions 2 and 4, especially when chains of alkyldiamine type are present, and by electron-releasing substituents (methoxy) in positions 7 and 8. The inactivity or the very low activity of title derivatives does not suggest interest in AIDS therapy. (C) 1999 Elsevier Science S.A. All rights reserved.