methyl 3-[2-(3-(4-biphenyl)ureido)phenyl]acrylate | 911840-04-5

• 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-(3-(4-biphenyl)ureido)phenyl]acrylate
• CAS: 911840-04-5
• 化学式: C₂₃H₂₀N₂O₃
• 分子量: 372.423
• InChiKey: AADRMVCPHZDAEK-UHFFFAOYSA-N

物化性质

• 沸点：
  479.7±38.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  67.43
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 3-[2-(3-(4-biphenyl)ureido)phenyl]acrylate 在 三乙胺 、 二溴三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 KYS05089
  参考文献：
  名称：

  In vivo evaluation of oral anti-tumoral effect of 3,4-dihydroquinazoline derivative on solid tumor

  摘要：

  An extension of our previously reported 3.4-dihydroquinazoline derivative is investigated. Oral anti-tumoral activity of 3,4-dihydroquinazoline derivative (KYS05090) as potent and selective T-type calcium channel blocker was in vivo evaluated against A549 xenograft in BALB/c(nu/nu) nude mice. The rate of tumor volume increment in mouse model with KY505090-treated group was remarkably slower than that of control group. With respect to tumor weight, it exhibited 60% and 67% tumor growth inhibition through oral administration of 1 and 5 mg/kg of bodyweight, respectively, compared to control and was more potent than paclitaxel (53%). In addition, KYS05090 (10 and 50 mg/kg, po) was found to have a marked analgesic effect in acetic acid-induced writhing test, whereas it did not show any effect on hot plate test. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.083
• 作为产物：
  描述：

  methyl 2-nitrocinnamate 在 tin(II) chloride dihdyrate 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 13.0h， 生成 methyl 3-[2-(3-(4-biphenyl)ureido)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

• 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.
• 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.