3-methyl-10-phenyl-5-deazaflavin | 69083-37-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-methyl-10-phenyl-5-deazaflavin
• 英文别名: 3-methyl-10-phenyl-5-deazaisoalloxazine；3-methyl-10-phenylpyrimido[4,5-b]quinoline-2,4(3H,10H)-dione；3-methyl-10-phenylpyrimido[4,5-b]quinoline-2,4-dione
• CAS: 69083-37-0
• 化学式: C₁₈H₁₃N₃O₂
• 分子量: 303.32
• InChiKey: MXTACMPGPLXHPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-10-phenyl-5-deazaflavin 、 环己醇 在 potassium carbonate 作用下， 反应 5.0h， 以38%的产率得到环己酮
  参考文献：
  名称：

  Yoneda, Fumio; Tsukuda, Kinshiro; Shinozuka, Kazuo, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 10, p. 3049 - 3056

  摘要：

  DOI：
• 作为产物：
  描述：

  6-anilino-3-methyluracil 在 偶氮二甲酸二乙酯 作用下， 以 环丁砜 、 溶剂黄146 为溶剂， 反应 1.5h， 生成 3-methyl-10-phenyl-5-deazaflavin
  参考文献：
  名称：

  Yoneda, Fumio; Tsukuda, Kinshiro; Shinozuka, Kazuo, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 10, p. 3049 - 3056

  摘要：

  DOI：

文献信息

• A new synthetic approach to 5-deazaflavin and 5-deaza-10-thiaflavin.
  作者：Xing CHEN、Kiyoshi TANAKA、Fumio YONEDA

  DOI：10.1248/cpb.38.612

  日期：——

  A novel, one-step synthesis of 5-deazaflavin developed, in which a [4+2]cycloaddition is presumably involved, to give the 5-deazaflavin derivative in moderate yield. This methodology was successfully applied to the stepwise preparation of its thio analogue, 5-deaza-10-thiaflavin, whose 1, 5-dihydro derivative was transformed into the corresponding sulfone in good yield.

  开发了一种新颖的一步合成5-去氟黄素的方法，其中可能涉及[4+2]环加成反应，以中等产率得到5-去氟黄素衍生物。这种方法成功应用于其硫类类似物5-去氟-10-硫黄素的逐步制备，其1,5-二氢衍生物转化为对应的磺酰胺，产率良好。
• A new synthetic method for the preparation of 5-deazaflavins and 5-deaza-10-oxaflavins
  作者：Xing Chen、Minako Nagata、Kiyoshi Tanaka、Fumio Yoneda

  DOI：10.1039/c39890000044

  日期：——

  The condensation of 6-chlorouracils with o-(substituted amino)benzyl alcohols and o-hydroxybenzyl alcohol gave directly 5-deazaflavin and 5-deaza-10-oxaflavin derivatives, respectively.

  6-氯尿嘧啶与邻-（取代的氨基）苄醇和邻-羟基苄醇的缩合分别直接得到5-脱氮杂黄酮和5-脱氮杂-10-氧杂黄酮衍生物。
• A new, general, and convenient synthesis of 5-deazaflavins (5-deazaisoalloxazines)
  作者：Tomohisa Nagamatsu、Yuko Hashiguchi、Mastsugu Higuchi、Fumio Yoneda

  DOI：10.1039/c39820001085

  日期：——

  The condensation of 6-substituted-aminouracils with o-halogenobenzaldehydes in dimethylformamide led to the formation of the corresponding 5-deazaflavins in a single step.

  6-取代的氨基尿嘧啶与邻卤代苯甲醛在二甲基甲酰胺中的缩合导致一步形成相应的5-脱氮黄素。
• 5-Deazaflavin derivatives as inhibitors of p53 ubiquitination by HDM2
  作者：Michael P. Dickens、Patricia Roxburgh、Andreas Hock、Mokdad Mezna、Barrie Kellam、Karen H. Vousden、Peter M. Fischer

  DOI：10.1016/j.bmc.2013.09.038

  日期：2013.11

  Based on previous reports of certain 5-deazaflavin derivatives being capable of activating the tumour suppressor p53 in cancer cells through inhibition of the p53-specific ubiquitin E3 ligase HDM2, we have conducted an structure-activity relationship (SAR) analysis through systematic modification of the 5-deazaflavin template. This analysis shows that HDM2-inhibitory activity depends on a combination of factors. The most active compounds (e. g., 15) contain a trifluoromethyl or chloro substituent at the deazaflavin C9 position and this activity depends to a large extent on the presence of at least one additional halogen or methyl substituent of the phenyl group at N10. Our SAR results, in combination with the HDM2 RING domain receptor recognition model we present, form the basis for the design of drug-like and potent activators of p53 for potential cancer therapy. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.
• CHEN, XING;NAGATA, MINAKO;TANAKA, KIYOSHI;YONEDA, FUMIO, J. CHEM. SOC. CHEM. COMMUN.,(1989) N, C. 44-45
  作者：CHEN, XING、NAGATA, MINAKO、TANAKA, KIYOSHI、YONEDA, FUMIO

  DOI：——

  日期：——