methyl 3-[2-((4-biphenyl)iminomethyleneamino)phenyl]acrylate | 839672-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-[2-((4-biphenyl)iminomethyleneamino)phenyl]acrylate
• 英文别名: methyl 3-[2-(4-biphenylyliminomethyleneamino)phenyl]acrylate；Methyl 3-[2-(4-biphenylyliminomethyleneamino)phenyl]acrylate
• CAS: 839672-50-3
• 化学式: C₂₃H₁₈N₂O₂
• 分子量: 354.408
• InChiKey: MGBTVKVOACFEHN-UHFFFAOYSA-N

物化性质

• 沸点：
  558.3±43.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  methyl 3-[2-((4-biphenyl)iminomethyleneamino)phenyl]acrylate 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 26.0h， 生成 KYS05089
  参考文献：
  名称：

  WO2008/136631

  摘要：

  公开号：
• 作为产物：
  描述：

  methyl 3-(2-aminophenyl)acrylate 在 三乙胺 、 二溴三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 methyl 3-[2-((4-biphenyl)iminomethyleneamino)phenyl]acrylate
  参考文献：
  名称：

  Anti-Cancer Activity of T-Type Calcium Channel Blocker In Vivo

  摘要：

  3,4-二氢喹唉1作为T型钙通道阻滞剂，在BALB/c-nu Slc裸鼠的A549异种移植模型中进行了体内评估，口服给药8毫克/千克体重显示出54%的肿瘤生长抑制作用，略低于多柔比星的68%活性。此外，还对该化合物对ICR小鼠的急性毒性进行了评估，得到了口服LD50值为1038毫克/千克体重。

  DOI：

  10.5012/bkcs.2010.31.11.3353

文献信息

• Anti-Cancer Activity of T-Type Calcium Channel Blocker In Vivo
  作者：Hang-Ah Park、Soo-Yeon Jung、So-Hyung Lee、Han-Byul Kang、Min-Sik Min、Jung-Ahn Kim、Dong-Joon Choo、Chun-Rim Oh、Young-Deuk Kim、Kyung-Tae Lee、Jae-Yeol Lee

  DOI：10.5012/bkcs.2010.31.11.3353

  日期：2010.11.20

  3,4-Dihydroquinazoline 1 as T-type calcium channel blocker was in vivo evaluated against A549 xenograft in BALB/c-nu Slc mice, which exhibited 54% tumor growth inhibition through oral administration of 8 mg/kg of body weight and was slightly less active than doxorubicin (68%). In addition, this compound was also profiled for its acute toxicity to ICR mice to afford oral $LD_50}$ value of 1,038 mg/kg of body weight.

  3,4-二氢喹唉1作为T型钙通道阻滞剂，在BALB/c-nu Slc裸鼠的A549异种移植模型中进行了体内评估，口服给药8毫克/千克体重显示出54%的肿瘤生长抑制作用，略低于多柔比星的68%活性。此外，还对该化合物对ICR小鼠的急性毒性进行了评估，得到了口服LD50值为1038毫克/千克体重。
• 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
  申请人：Lee Jae Yeol

  公开号：US20100120803A1

  公开（公告）日：2010-05-13

  The present invention relates to 3,4-dihydroquinazoline derivatives, a process of preparing them and a pharmaceutical composition including them. The 3,4-dihydroquinazoline derivatives of the present invention have excellent T-type calcium channel blocking effect and anti-cancer activity.

  本发明涉及3,4-二氢喹唑啉衍生物、其制备方法以及包括它们的药物组合物。本发明的3,4-二氢喹唑啉衍生物具有出色的T型钙通道阻滞效果和抗癌活性。
• 3,4-dihydroquinazoline derivatives
  申请人：Dongwoo Syntech Co., Ltd.

  公开号：US08168646B2

  公开（公告）日：2012-05-01

  Disclosed are 3,4-dihydroquinazoline derivatives of formula (I), a process of preparing them and a pharmaceutical composition including them. The 3,4-dihydroquinazoline derivatives of the present invention have excellent T-type calcium channel blocking effect and anti-cancer activity

  本发明涉及公式（I）的3,4-二氢喹唑啉衍生物，其制备方法以及包括它们的药物组合物。本发明的3,4-二氢喹唑啉衍生物具有优异的T型钙通道阻滞效果和抗癌活性。
• Antitumor activity of 3,4-dihydroquinazoline dihydrochloride in A549 xenograft nude mice
  作者：Soo Yeon Jung、So Hyung Lee、Han Byul Kang、Hang Ah Park、Sun Ki Chang、Jungahn Kim、Dong Joon Choo、Chun Rim Oh、Young Deuk Kim、Ji Hyung Seo、Kyung-Tae Lee、Jae Yeol Lee

  DOI：10.1016/j.bmcl.2010.09.020

  日期：2010.11

  In the previous article we have reported that 3,4-dihydroquinazoline 1 is a potent and selective T-type calcium channel blocker that exhibited strong anti-cancer activity in vitro. Compound 1 center dot 2HCl was further in vivo evaluated against A549 xenograft in BALB/c nude mice, which exhibited 49% tumor-weight inhibition through intravenous administration of 2 mg/kg of body weight and was more potent than doxorubicin. Moreover, compound 1 center dot 2HCl has an oral bioavailability of 98% with LD(50) values of 693 mg/kg (po route) and 40.0 mg/kg (iv route) of body weight. In addition, its efficient scale-up synthetic method was developed. (C) 2010 Elsevier Ltd. All rights reserved.