3-Amino-1-oxo-2-phenyl-4a,5,6,7-tetrahydropyrrolo[1,2-c]pyrimidine-4-carbonitrile | 177662-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 3-Amino-1-oxo-2-phenyl-4a,5,6,7-tetrahydropyrrolo[1,2-c]pyrimidine-4-carbonitrile
• 英文别名: 3-amino-1-oxo-2-phenyl-4a,5,6,7-tetrahydropyrrolo[1,2-c]pyrimidine-4-carbonitrile
• CAS: 177662-77-0
• 化学式: C₁₄H₁₄N₄O
• 分子量: 254.291
• InChiKey: LPCMNNNLRNOHCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Amino-1-oxo-2-phenyl-4a,5,6,7-tetrahydropyrrolo[1,2-c]pyrimidine-4-carbonitrile 在 一水合肼 作用下， 以 乙醇 、 苯 为溶剂， 反应 10.0h， 生成 7,13-Dioxo-8-phenyl-6,8,10,12-tetrazatricyclo[7.4.0.02,6]trideca-1(9),10-diene-11-carbohydrazide
  参考文献：
  名称：

  New pyrimido[5,4-e]pyrrolo[1,2-c]pyrimidines: Synthesis, 2D-QSAR, anti-inflammatory, analgesic and ulcerogenicity studies

  摘要：

  New pyrimido[5,4-e]pyrrolo[1,2-c]pyrimidines were synthesized. A series of ylidene carbohydrazides 14a-i, and hydrazonate 15, were obtained from the prepared 3-carbohydrazide derivative 13. Pyrazole derivatives 12, 16a,b, 18, 19, 20, were also prepared through different reactions. The anti-inflammatory and analgesic activities of all new compounds were evaluated and most of them exerted comparable activity to indomethacin and celecoxib. Ulcer indexes for the most active compounds were calculated and most of them showed less ulcerogenic effect than the reference drugs. The most potent anti-inflammatory compound 12 showed an IC50 of 6.00 mu mol/kg and low ulcer index. COX-1/COX-2 activity ratio of compounds 12 and 16b showed almost equal inhibitory effect on both isoenzymes. 2D-QSAR studies revealed good predictive and statistically significant QSAR models. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.048
• 作为产物：
  描述：

  3-imino-1-oxo-2-phenyl-6,7-dihydro-5H-pyrrolo[1,2-c]pyrimidine-4-carbonitrile 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 3-Amino-1-oxo-2-phenyl-4a,5,6,7-tetrahydropyrrolo[1,2-c]pyrimidine-4-carbonitrile
  参考文献：
  名称：

  New pyrimido[5,4-e]pyrrolo[1,2-c]pyrimidines: Synthesis, 2D-QSAR, anti-inflammatory, analgesic and ulcerogenicity studies

  摘要：

  New pyrimido[5,4-e]pyrrolo[1,2-c]pyrimidines were synthesized. A series of ylidene carbohydrazides 14a-i, and hydrazonate 15, were obtained from the prepared 3-carbohydrazide derivative 13. Pyrazole derivatives 12, 16a,b, 18, 19, 20, were also prepared through different reactions. The anti-inflammatory and analgesic activities of all new compounds were evaluated and most of them exerted comparable activity to indomethacin and celecoxib. Ulcer indexes for the most active compounds were calculated and most of them showed less ulcerogenic effect than the reference drugs. The most potent anti-inflammatory compound 12 showed an IC50 of 6.00 mu mol/kg and low ulcer index. COX-1/COX-2 activity ratio of compounds 12 and 16b showed almost equal inhibitory effect on both isoenzymes. 2D-QSAR studies revealed good predictive and statistically significant QSAR models. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.048

文献信息

• Novel heterocyclic-fused pyrimidine derivatives: Synthesis, molecular modeling and pharmacological screening
  作者：Reem K. Arafa、Mai S. Nour、Nehad A. El-Sayed

  DOI：10.1016/j.ejmech.2013.08.042

  日期：2013.11

  Novel heterocyclic-fused pyrimidines viz pyrrolo[1,2-c]pyrimidines 4–8, pyrimido[5,4-e]pyrrolo[1,2-c]pyrimidines 9–14, pyrimido[4′,5′:4,5]pyrimido[1,6-a]azepines 16–18, pyrrolo[1′,2′:1,6]pyrimido[4,5-d][1,3]thiazines 19a,b and 1,3-thiazino[4′,5′:4,5]pyrimido[1,6-a]-azepine 19c were designed and synthesized as potential anticancer agents. In this investigation all the newly synthesized compounds were

  新的杂环稠合嘧啶即吡咯并[1,2 -c ]嘧啶4 - 8，嘧啶并[5,4- ë ]吡咯并[1,2- c ^ ]嘧啶9 - 14，嘧啶并[4'，5'：4， 5] pyrimido [ 1,6 - a ]氮杂16 16-18，吡咯并[1，，2'：1,6] pyrimido [4,5- d ] [1,3]噻嗪19a，b和1,3-噻嗪[4'，5'：4,5]嘧啶基[1,6- a ] -a庚因19c被设计和合成为潜在的抗癌药。在这项研究中，所有新合成的化合物都针对MCF-7乳腺癌细胞系进行了细胞毒性筛选。此外，激酶抑制测定法对化合物进行5，7，9和18分别抵靠非受体和受体酪氨酸激酶的c-Src和VEGFR。所测试的化合物对c-Src的抑制作用比VEGFR更强，在18种化合物中观察到最高的活性。显示出81％的c-Src活性抑制。最后，用c-Src和VEGFR进行了分子对接，以试图模拟和理解这些小分子与激
• Synthesis, analgesic and anti-inflammatory activities evaluation of some bi-, tri- and tetracyclic condensed pyrimidines
  作者：Kamilia M. Amin、Mona M. Hanna、Hanan E. Abo-Youssef、Riham F. George

  DOI：10.1016/j.ejmech.2009.06.028

  日期：2009.11

  Novel series of bicyclic pyrrolo[1,2-cipyrimidines 3a-g, 5, 6a, b, and 7a, b, tricyclic pyrimido[5,4-elpyrrolo[1,2-c]pyrimidines 8a-c, 9a-g, 13a-c, 17,18a, b, 19, 20a,b and 21 and tetracyclic condensed pyrimidines 14, 22 and 23 were synthesized through different chemical reactions. Structures of all synthesized pyrimidine derivatives were supported by spectral and elemental analyses. Analgesic activity evaluation was carried out using acetic acid-induced writhing assay, and all compounds exerted comparable activity to indomethacin. The anti-inflammatory activity evaluation was performed using carrageenan-induced paw edema in rats, the potency of the bicyclic derivatives 3a-f and 7b revealed comparable activity to indomethacin without gastric ulceration. The tricyclic derivatives 13a and 20a exerted good activity, however, they induced gastric ulcers while 13b and 13c showed moderate activity without ulceration. In case of tetracyclic derivatives, compound 14 exhibited the highest potency and safety profile. (C) 2009 Elsevier Masson SAS. All rights reserved.