2-amino-3-cyano-5-methyl-4-phenylpyrrole | 54153-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-amino-3-cyano-5-methyl-4-phenylpyrrole
• 英文别名: 2-amino-5-methyl-4-phenyl-1H-pyrrole-3-carbonitrile
• CAS: 54153-52-5
• 化学式: C₁₂H₁₁N₃
• 分子量: 197.239
• InChiKey: XBTFZXGMLHPKFI-UHFFFAOYSA-N

物化性质

• 沸点：
  466.9±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-3-cyano-5-methyl-4-phenylpyrrole 在 sodium ethanolate 、 sodium nitrite 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 4-Amino-8-cyano-6-methyl-7-phenylpyrrolo[2,1-c][1,2,4]triazine-3-carboxamide
  参考文献：
  名称：

  2-重氮吡咯的吡咯并[2,1-c] [1,2,4]三嗪：合成和抗增殖活性。

  摘要：

  吡咯并[2,1-c] [1,2,4]三嗪4a-g直接从2-重氮吡咯1a和b与β-二酮，β-腈和β-二腈的钠盐反应而获得。仅当2-重氮吡咯与氰基乙酸乙酯偶联时，才可能与吡咯并三嗪一起分离出中间3，后者又环化成标题环系统。美国国家癌症研究所评估了吡咯并三嗪4a-e对60种人类癌细胞系的细胞毒性活性，其中一些表现出对多种癌细胞系生长的抑制作用，通常在10（-5）M水平在某些情况下，浓度为微摩尔。

  DOI：

  10.1016/s0223-5234(02)01339-9

文献信息

• Pyrrolo[2,1-d][1,2,3,5]tetrazine-4(3h)-ones, a new class of azolotetrazines with potent antitumor activity
  作者：Patrizia Diana、Paola Barraja、Antonino Lauria、Alessandra Montalbano、Anna Maria Almerico、Gaetano Dattolo、Girolamo Cirrincione

  DOI：10.1016/s0968-0896(03)00145-7

  日期：2003.5.29

  Pyrrolo[2,1-d][1,2,3,5]tetrazinones 10a-o, compounds that hold the deaza skeleton of the antitumor drug temozolomide, were prepared by reaction of 2-diazopyrroles 9 and isocyanates. Such a synthetic route represents, among those leading to azolo-tetrazinones reported so far, the only possible one since attempts to cyclize to the title ring system 2-amino-1-carbamoylpyrroles 11 or the mono substituted 2-triazenopyrrole 12 failed. Compounds 10 were screened at the National Cancer Institute (NCI) for their activity against a panel of about 60 human tumor cell lines. Most of them possess remarkable antineoplastic activity having 6150 values in the low micromolar or sub-micromolar range and reaching, in the case of compound 10d, nanomolar concentrations. The most sensitive cell lines were MDA-N and MDA-MB-435 of the breast sub-panel, and SR, K-562, HL60 (TB) and CCRF-CEM of the leukaemia sub-panel. SAR evaluation and COMPARE computations indicate, for compounds 10, a mechanism of action different from that of temozolomide. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Neue Synthese von substituierten 4-Amino-chinazolinen und deren Heteroanalogen
  作者：K. Gewald、H. Sch�fer、K. Eckert、T. Jeschke

  DOI：10.1002/prac.19963380144

  日期：——

  N-Chloracetyl-anthranilonitriles react with potassium thiocyanate in the presence of alcohol to the (4-amino-quinazolin-2-yl-thio)-acetic acid ester (5). In the presence of water or primary amine the acetic acid derivative (6) or the acetic acid amide derivatives (7) are obtained. 2,4-Diamino-quinazolines (8) arise if vigorous reaction conditions are employed. With 2-chloracetylamino-cyclopent-1-en-carbonitrile as starting material the pyrimidines (11) are formed from the reaction with potassium thiocyanate. Analogously, (4-pyrimidyl-2-yl-seleno)-acetic acid ester (12) and (thiazolo[4,5d]pyrimid-2-yl-seleno)-acetic acid derivatives (16)can be prepared with potassium selenocyanate. N-Chloracetyl derivatives of 5-membered heterocycles with enamino-nitrile structure (13, 15, 18, 20) react with potassium thiocyanate to yield thieno[2,3-d]-, thiazolo[4,5-d]-, pyrrolo[2,3-d]-, furo[2,3-d]and pyrazolo[4,3-d]pyrimidines (14, 16, 19a, 19b, 21).
• Pyrrolo[2,1-d][1,2,3,5]tetrazines, a New Class of Azolotetrazines Related to the Antitumor Drug Temozolomide
  作者：Patrizia Diana

  DOI：10.1055/s-1999-3628

  日期：1999.12
• 5,6-Condensed 3-nitropyridines from heterocyclic amines and nitromalonaldehyde
  作者：H. Sch�fer、K. Gewald、M. Schmidt

  DOI：10.1007/bf00515347

  日期：1983.11
• SHEFER, X.;GEVALD, K.;SHMIDT, M., XIMIYA GETEROTSIKL. SOEDIN., 1983, N 11, 1471-1475
  作者：SHEFER, X.、GEVALD, K.、SHMIDT, M.

  DOI：——

  日期：——