(E)-3-(2-Phenyliminomethyleneamino-phenyl)-acrylic acid methyl ester | 139210-05-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(2-Phenyliminomethyleneamino-phenyl)-acrylic acid methyl ester
• 英文别名: Methyl 3-[2-(phenyliminomethyleneamino)phenyl]acrylate
• CAS: 139210-05-2
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: BZFSBORDSWYJLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-Phenyliminomethyleneamino-phenyl)-acrylic acid methyl ester 以 甲苯 为溶剂， 反应 24.0h， 生成 2-anilino-3-carbomethoxyquinoline
  参考文献：
  名称：

  C=C-conjugated carbodiimides as 2-aza dienes in intramolecular [4+2] cycloadditions. One-pot preparation of quinoline, .alpha.-carboline, and quinindoline derivatives

  摘要：

  Iminophosphoranes 2 derived from o-aminostyrenes react with aryl isocyanates to give the corresponding carbodiimides 13 which by thermal treatment at 160-degrees-C undergo 6-pi-electrocyclization to give quinoline derivatives 14. However, the reaction with styryl isocyanates leads to alpha-carbolines 19 through the intermediate carbodiimides 15 which undergo a tandem intramolecular hetero-Diels-Alder cycloaddition/aromatization process to give 19. Similarly, related alpha-carbolines 20-22 can be obtained from the reaction of iminophosphoranes derived from ortho-substituted anilines containing an unsaturated side chain with styryl isocyanates. Iminophosphorane 6a, derived from o-butadienylaniline, and related 10 and 12 react with aryl isocyanates under the same reaction conditions to give quinindoline derivatives 25-27, respectively. Finally, iminophosphoranes 2 and 6 by reaction with ketenes lead directly to quinolines 32 and benzo[b]carbazoles 33, respectively.

  DOI：

  10.1021/jo00029a026
• 作为产物：
  描述：

  (E)-3-[2-(3-Phenyl-ureido)-phenyl]-acrylic acid methyl ester 在 triphenylphosphine dibromide 1:1 addition complex 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-(2-Phenyliminomethyleneamino-phenyl)-acrylic acid methyl ester
  参考文献：
  名称：

  T-type Ca2+ channel blockers suppress the growth of human cancer cells

  摘要：

  In order to further clarify the role of T-type Ca2+ channels in cell proliferation, we have measured the growth inhibition of human cancer cells by using our potent T-type Ca2+ channel blockers. As a result, KYS05090, a most potent T-type Ca2+ channel blocker, was found to be as potent as doxorubicin against some human cancer cells without acute toxicity. Therefore, this letter provides the biological results that T-type calcium channel is important in regulating the important cellular phenotype transition leading to cell proliferation, and thus novel T-type Ca2+ channel blocker presents new prospects for cancer treatment. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.034

文献信息

• A cascade reaction of o -alkenylphenyl carbodiimides with isocyanides by copper catalysis: direct construction of 4,5-dihydroimidazo[1,5- a ]quinazolines
  作者：Wenyan Hao、Xiaoyan Sang、Yunsheng Xiao、Mingzhong Cai

  DOI：10.1016/j.tetlet.2016.08.006

  日期：2016.9

  efficient method for the synthesis of 4,5-dihydroimidazo[1,5-a]quinazolines derivatives by copper catalyzed cascade reaction of o-alkenylphenyl carbodiimides with isocyanides has been developed. Moderate to good yields could be obtained by using CuI as the catalyst and K3PO4 as the base. This reaction initially proceeds through a formal [3+2] cycloaddition and followed by intramolecular conjugate addition annulation

  开发了一种通过邻位烯基苯基碳二亚胺与异氰酸酯的铜催化级联反应合成4,5-二氢咪唑并[1,5- a ]喹唑啉衍生物的有效方法。通过使用CuI作为催化剂，并使用K 3 PO 4作为碱，可以获得中等至良好的产率。该反应首先通过正式的[3 + 2]环加成反应进行，然后进行分子内偶联物加成环化反应。
• Synthesis and SAR Study of T-Type Calcium Channel Blockers. Part II
  作者：Yun Jeong Choe、Han Na Seo、Soo Yeon Jung、Hyewhon Rhim、Jungahn Kim、Dong Joon Choo、Jae Yeol Lee

  DOI：10.1002/ardp.200800079

  日期：2008.10

  3,4‐Dihydroquinazoline derivatives have been known to be the novel and potent T‐type calcium channel blockers. From a systematic variation of 3,4‐dihydroquinazoline derivative 5c (KYS05043), plausible SAR results were established. It was revealed that a 5‐(dimethylamino)pentylamino group at R1, a biphenyl group at R2, and a benzyl amido group at R3 in the 3,4‐dihydroquinazoline backbone are closely

  已知 3,4-二氢喹唑啉衍生物是新型有效的 T 型钙通道阻滞剂。根据 3,4-二氢喹唑啉衍生物 5c (KYS05043) 的系统变异，建立了合理的 SAR 结果。结果表明，3,4-二氢喹唑啉骨架中R1的5-(二甲氨基)戊氨基、R2的联苯基和R3的苄基氨基与通道选择性(T/N型)密切相关。以及基于 6k (KYS05090) 发现的效力。
• 3,4-Dihydroquinazoline derivatives as T-type calcium channel blockers and method of preparing the same
  申请人：Lee Yong Sup

  公开号：US20050197351A1

  公开（公告）日：2005-09-08

  The present invention relates to 3,4-dihydroquinazoline derivatives as T-type calcium channel blockers and a method of preparing the same. The present invention further relates to a composition comprising the same. The composition comprising the 3,4-dihydroquinazoline derivatives of the present invention can be effectively used for preventing and treating angina pectoris, high blood pressure, myocardial disease, pain and epilepsy by blocking the T-type calcium channel.

  本发明涉及作为T型钙通道阻滞剂的3,4-二氢喹唑啉衍生物及其制备方法。本发明还涉及包含该衍生物的组合物。本发明的3,4-二氢喹唑啉衍生物组成的组合物可以通过阻断T型钙通道有效地用于预防和治疗心绞痛、高血压、心肌疾病、疼痛和癫痫。
• 3,4-dihydroquinazoline derivatives as T-type calcium channel blockers and method of preparing the same
  申请人：Korea Institute of Science and Technology

  公开号：US07271260B2

  公开（公告）日：2007-09-18

  The present invention relates to 3,4-dihydroquinazoline derivatives as T-type calcium channel blockers and a method of preparing the same. The present invention further relates to a composition comprising the same. The composition comprising the 3,4-dihydroquinazoline derivatives of the present invention can be effectively used for preventing and treating angina pectoris, high blood pressure, myocardial disease, pain and epilepsy by blocking the T-type calcium channel.

  本发明涉及作为T型钙通道阻滞剂的3,4-二氢喹唑啉衍生物及其制备方法。本发明还涉及包含该衍生物的组合物。本发明中包含3,4-二氢喹唑啉衍生物的组合物可以通过阻塞T型钙通道有效地用于预防和治疗心绞痛、高血压、心肌病、疼痛和癫痫。
• T-type Ca2+ channel blockers suppress the growth of human cancer cells
  作者：Jae Ho Heo、Han Na Seo、Yun Jeong Choe、Sujin Kim、Chun Rim Oh、Young Deuk Kim、Hyewhon Rhim、Dong Joon Choo、Jungahn Kim、Jae Yeol Lee

  DOI：10.1016/j.bmcl.2008.06.034

  日期：2008.7

  In order to further clarify the role of T-type Ca2+ channels in cell proliferation, we have measured the growth inhibition of human cancer cells by using our potent T-type Ca2+ channel blockers. As a result, KYS05090, a most potent T-type Ca2+ channel blocker, was found to be as potent as doxorubicin against some human cancer cells without acute toxicity. Therefore, this letter provides the biological results that T-type calcium channel is important in regulating the important cellular phenotype transition leading to cell proliferation, and thus novel T-type Ca2+ channel blocker presents new prospects for cancer treatment. (C) 2008 Elsevier Ltd. All rights reserved.