1,3-diethyl-5-(3-phenylallylidene)-2-thioxodihydropyrimidine-4,6-dione | 204260-53-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,3-diethyl-5-(3-phenylallylidene)-2-thioxodihydropyrimidine-4,6-dione
• 英文别名: 1,3-diethyl-5-(3-phenylallyl)-2-thiobarbituric acid；DDD00124821；5-Cinnamylidene-1,3-diethyl-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 204260-53-7
• 化学式: C₁₇H₁₈N₂O₂S
• 分子量: 314.408
• InChiKey: WARNILUNFMPQTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-二乙基硫脲 在 吡啶 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 1,3-diethyl-5-(3-phenylallylidene)-2-thioxodihydropyrimidine-4,6-dione
  参考文献：
  名称：

  Design and synthesis of novel thiobarbituric acid derivatives targeting both wild-type and BRAF-mutated melanoma cells

  摘要：

  A series of novel thio-and seleno-barbituric acid derivatives were synthesized by varying the substituents at N1 and N3 (ethyl, methyl, allyl, and phenyl), and C5 tethered with dienyl and trienyl moieties attached to substituents such as phenyl, 2-furanyl, 2-thiophenyl, l-naphthyl, and 3-pyridyl. The cytotoxic potential of these derivatives was evaluated by using MTT assay against melanoma cell lines expressing either wild-type (CHL-1) or mutant (UACC 903) BRAF gene. Among all, 2b and 8b were identified as the most potent compounds. Both 2b and 8b inhibited viability of various melanoma cells and induced cell death as evidenced by Live and Dead assay. Western blot analysis showed that they induce PARP cleavage and inhibit anti-apoptotic Bcl-2, Bcl-xL and Survivin in a dose-dependent manner within 24 h of the treatment. Novel thiobarbituric acid analogs also inhibited viability of various other solid tumor cell lines, such as pancreatic, breast, and colon. Overall, 2b, 2d, and 8b emerged as the most effective compounds and make good leads for the development of future therapeutic agents. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.006

文献信息

• 一种含巴比妥类结构的化合物及其制备方法与应用
  申请人：武汉大学

  公开号：CN117624062A

  公开（公告）日：2024-03-01

  本发明公开了一种含巴比妥类结构的化合物及其制备方法与应用，所述含巴比妥类结构的化合物的结构式如下，所述方法包括：在惰性气体保护下，将芳香醛类化合物溶解于有机溶剂中，加入巴比妥酸或其衍生物混匀，并加入碱作为催化剂于室温下反应，经后处理后得到。该化合物可作为光引发剂，在可见光区展现出强的吸收和高的摩尔消光系数，且合成方法简单，储存稳定性好，对丙烯酸酯树脂表现出高的引发效率和良好的光漂白能力。#imgabs0#
• Design and synthesis of novel thiobarbituric acid derivatives targeting both wild-type and BRAF-mutated melanoma cells
  作者：Srinivasa Rao Ramisetti、Manoj K. Pandey、Sang Y. Lee、Deepkamal Karelia、Satya Narayan、Shantu Amin、Arun K. Sharma

  DOI：10.1016/j.ejmech.2017.11.006

  日期：2018.1

  A series of novel thio-and seleno-barbituric acid derivatives were synthesized by varying the substituents at N1 and N3 (ethyl, methyl, allyl, and phenyl), and C5 tethered with dienyl and trienyl moieties attached to substituents such as phenyl, 2-furanyl, 2-thiophenyl, l-naphthyl, and 3-pyridyl. The cytotoxic potential of these derivatives was evaluated by using MTT assay against melanoma cell lines expressing either wild-type (CHL-1) or mutant (UACC 903) BRAF gene. Among all, 2b and 8b were identified as the most potent compounds. Both 2b and 8b inhibited viability of various melanoma cells and induced cell death as evidenced by Live and Dead assay. Western blot analysis showed that they induce PARP cleavage and inhibit anti-apoptotic Bcl-2, Bcl-xL and Survivin in a dose-dependent manner within 24 h of the treatment. Novel thiobarbituric acid analogs also inhibited viability of various other solid tumor cell lines, such as pancreatic, breast, and colon. Overall, 2b, 2d, and 8b emerged as the most effective compounds and make good leads for the development of future therapeutic agents. (C) 2017 Elsevier Masson SAS. All rights reserved.