4-氯-2,5-二甲基-7-(2,4,6-三甲基苯基)-7H-吡咯并[2,3-d]嘧啶 | 157286-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4-氯-2,5-二甲基-7-(2,4,6-三甲基苯基)-7H-吡咯并[2,3-d]嘧啶
• 中文别名: 4-氯-7-均三苯基-2,5-二甲基-7H-吡咯[2,3-D]嘧啶
• 英文名称: 4-chloro-2,5-dimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo-[2,3-d]pyrimidine
• 英文别名: 4-chloro-2,5-dimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidine；4-chloro-2,5-dimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[3,2-e]pyrimidine；4-Chloro-7-mesityl-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidine；4-chloro-2,5-dimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidine
• CAS: 157286-81-2
• 化学式: C₁₇H₁₈ClN₃
• 分子量: 299.803
• InChiKey: CGLDYVRQHDEHPG-UHFFFAOYSA-N

物化性质

• 沸点：
  335.4±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 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：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-氯-2,5-二甲基-7-(2,4,6-三甲基苯基)-7H-吡咯并[2,3-d]嘧啶 在 palladium on activated charcoal 氘 作用下， 以 二甲基亚砜 、 乙酸乙酯 为溶剂， 130.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 [2H]butyl[2,5-dimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]ethylamine
  参考文献：
  名称：

  Synthesis and Oral Efficacy of a 4-(Butylethylamino)pyrrolo[2,3-d]pyrimidine:  A Centrally Active Corticotropin-Releasing Factor₁ Receptor Antagonist

  摘要：

  The syntheses of a centrally active nonpeptide CRF1 receptor antagonist 2, butylethyl[2,5-dimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine (CP-154,526), and its analogs 11-14 and [H-3]-2 are reported. The in vitro CRF1 receptor binding affinity in the series 2, the pharmacokinetic properties of 2 in rats, and the anxiolytic-like effects of orally administered 2 are presented.

  DOI：

  10.1021/jm960861b
• 作为产物：
  描述：

  异亚丙基丙二腈 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 磷酸 、 溶剂黄146 、 三氯氧磷 作用下， 反应 33.75h， 生成 4-氯-2,5-二甲基-7-(2,4,6-三甲基苯基)-7H-吡咯并[2,3-d]嘧啶
  参考文献：
  名称：

  Synthesis and Oral Efficacy of a 4-(Butylethylamino)pyrrolo[2,3-d]pyrimidine:  A Centrally Active Corticotropin-Releasing Factor₁ Receptor Antagonist

  摘要：

  The syntheses of a centrally active nonpeptide CRF1 receptor antagonist 2, butylethyl[2,5-dimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine (CP-154,526), and its analogs 11-14 and [H-3]-2 are reported. The in vitro CRF1 receptor binding affinity in the series 2, the pharmacokinetic properties of 2 in rats, and the anxiolytic-like effects of orally administered 2 are presented.

  DOI：

  10.1021/jm960861b

文献信息

• Synthesis, Corticotropin-Releasing Factor Receptor Binding Affinity, and Pharmacokinetic Properties of Triazolo-, Imidazo-, and Pyrrolopyrimidines and -pyridines
  作者：Robert J. Chorvat、Rajagopal Bakthavatchalam、James P. Beck、Paul J. Gilligan、Richard G. Wilde、Anthony J. Cocuzza、Frank W. Hobbs、Robert S. Cheeseman、Matthew Curry、Joseph P. Rescinito、Paul Krenitsky、Dennis Chidester、Jerry A. Yarem、John D. Klaczkiewicz、C. Nicholas Hodge、Paul E. Aldrich、Zelda R. Wasserman、Christine H. Fernandez、Robert Zaczek、Lawrence W. Fitzgerald、Shiew-Mei Huang、Helen L. Shen、Y. Nancy Wong、Ben M. Chien、Check Y. Quon、Argyrios Arvanitis

  DOI：10.1021/jm980224g

  日期：1999.3.1

  The synthesis and CRF receptor binding affinities of several new series of N-aryltriazolo- and -imidazopyrimidines and -pyridines are described. These cyclized systems were prepared from appropriately substituted diaminopyrimidines or -pyridines by nitrous acid, orthoester, or acyl halide treatment. Variations of amino (ether) pendants and aromatic substituents have defined the structure-activity relationships

  描述了几种新系列的N-芳基三唑-和-咪唑并嘧啶和-吡啶的合成和CRF受体结合亲和力。这些环化体系是由适当取代的二氨基嘧啶或-吡啶通过亚硝酸，原酸酯或酰卤处理制得的。氨基（醚）侧基和芳族取代基的变化定义了这些系列的结构-活性关系，并导致鉴定出多种高亲和力试剂（Ki's <10 nM）。基于该性质和亲脂性差异，最初选择了其中的六个化合物（4d，i，n，x，8k，9a）用于大鼠药代动力学（PK）研究。良好的口服生物利用度，高血浆水平以及四种化合物的持续时间（4d，i，n，x）提示在静脉内和口服给药后都对狗进行了进一步的PK研究。这项工作的结果表明4i，x具有我们认为是潜在治疗剂所必需的特性，并且已选择4i1进行进一步的药理研究，并将在适当时候进行报道。
• Pyrrolopyrimidines as CRF antagonists
  申请人：Pfizer Inc

  公开号：US06765008B1

  公开（公告）日：2004-07-20

  The compounds of the formula wherein R1, R2, R3, R4, R5 and R6 are as defined herein, are useful in the treatment of stress-related and other diseases. These compounds have corticotropin-releasing factor antagonist activity and as such are of use in the treatment of stress and anxiety related, and other disorders.

  式中R1、R2、R3、R4、R5和R6所定义的化合物在治疗与压力相关和其他疾病方面是有用的。这些化合物具有促肾上腺皮质激素释放因子拮抗剂活性，因此在治疗与压力、焦虑相关和其他疾病方面有用。
• Aminoalkyl substituted pyrrolo &lsqb;3,2-E&rsqb;pyridine and pyrollo &lsqb;2,3-b&rsqb;pyrimidine derivatives: modulators of CRF1 receptors
  申请人：Neurogen Corporation

  公开号：US06310063B1

  公开（公告）日：2001-10-30

  Disclosed are compounds of the formula: wherein Ar, Q1, Q2, R1, W and X are substituents as defined herein, which compounds are water-soluble CRF1 receptor antagonists, and are therefore useful for the treatment of psychiatric disorders and neurological diseases, including major depression, anxiety-related disorders, post-traumatic stress disorder, supranuclear palsy and feeding disorders, as well as treatment of immunological, cardiovascular or heart-related diseases and colonic hypersensitivity associated with psychopathological disturbance and stress.

  揭示了以下公式的化合物：其中Ar、Q1、Q2、R1、W和X是如下所定义的取代基，这些化合物是水溶性CRF1受体拮抗剂，因此可用于治疗精神障碍和神经系统疾病，包括重大抑郁症、焦虑相关障碍、创伤后应激障碍、上核性麻痹和进食障碍，以及治疗与心理病理障碍和压力相关的免疫、心血管或心脏相关疾病和结肠过敏相关的过敏性。
• Martarello; Kilts; Ely, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S312-S314
  作者：Martarello、Kilts、Ely、Owens、Nemeroff、Goodman

  DOI：——

  日期：——
• PYRROLOPYRIMIDINES AS CRF ANTAGONISTS
  申请人：PFIZER INC.

  公开号：EP0674641B1

  公开（公告）日：1999-03-03