Tetraethyl 4,4'-Dithiobis(N-benzoyl-L-glutamate) | 56527-28-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Tetraethyl 4,4'-Dithiobis(N-benzoyl-L-glutamate)
• 英文别名: diethyl (2S)-2-[[4-[[4-[[(2S)-1,5-diethoxy-1,5-dioxopentan-2-yl]carbamoyl]phenyl]disulfanyl]benzoyl]amino]pentanedioate
• CAS: 56527-28-7
• 化学式: C₃₂H₄₀N₂O₁₀S₂
• 分子量: 676.809
• InChiKey: RJJZJZZLRKINLX-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  46.0
• 可旋转键数：
  19.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  163.4
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Tetraethyl 4,4'-Dithiobis(N-benzoyl-L-glutamate) 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 9.25h， 生成 2-desamino-5,8-dideaza-10-thiafolic acid
  参考文献：
  名称：

  Comparison of the biological effects of selected 5,8-dideazafolate analogs with their 2-desamino counterparts

  摘要：

  Three new 5,8-dideaza analogues of folic acid devoid of an amino group at position 2 have been prepared by using synthetic routes patterned after earlier methodologies. They were 2-desamino-5,8-dideazaisofolic acid, 2b, 2-desamino-10-thia-5,8-dideazafolic acid, 2c, and 2-desamino-10-oxa-5,8-dideazafolic acid, 2d. These compounds were found to be 4-6-fold more cytoxic toward L1210 leukemia cells than their 2-NH2 counterparts and to be poor inhibitors of mammalian thymidylate synthase. However, they were only 1.5-3-fold less inhibitory toward dihydrofolate reductase than the analogous compounds containing a 2-NH2 group. The known thymidylate synthase inhibitors 2-desamino-10-propargyl-5,8-dideazafolic acid and 10-propargyl-5,8-dideazafolic acid were included in this study for purposes of comparison.

  DOI：

  10.1021/jm00124a019

文献信息

• Quinazoline antifolate thymidylate synthase inhibitors: bridge modifications and conformationally restricted analogs in the C2-methyl series
  作者：Peter R. Marsham、Ann L. Jackman、Anthony J. Hayter、Melanie R. Daw、Jayne L. Snowden、Brigid M. O'Connor、Joel A. M. Bishop、A. Hilary Calvert、Leslie R. Hughes

  DOI：10.1021/jm00111a042

  日期：1991.7

  N10 bridge has been replaced by the reversed N9,C10 unit. This series was extensively studied by incorporating further substituents at N9 and C10 as well as by modifications to the p-aminobenzoate ring. The C2-methylquinazoline analogues 29, 30, and 31 containing the methyleneoxa, methylenethia, and thia bridge units were also synthesized. In general these isosteric replacements of the bridge unit

  已经制备了几种基于C2-甲基喹唑啉的抗叶酸剂，其中C9，N10桥被反向的N9，C10单元代替。通过在N9和C10处引入其他取代基以及对对氨基苯甲酸酯环的修饰，对该系列进行了广泛的研究。还合成了含有亚甲基氧杂，亚甲基硫杂和硫杂桥单元的C 2-甲基喹唑啉类似物29、30和31。通常，亲本C 2-甲基-N 10-炔丙基喹唑啉抗叶酸2中桥单元的这些等排替代物作为分离的胸苷酸合酶（TS）抑制剂的效力要低得多，但几种至少与培养中的L1210细胞生长抑制剂一样有效。对氨基苯甲酸酯环与双环系统75和76的融合也降低了对TS的活性，但又产生了高度细胞毒性的化合物。
• Synthesis and in vitro antitumor activity of new quinoxaline derivatives
  作者：Paola Corona、Antonio Carta、Mario Loriga、Gabriella Vitale、Giuseppe Paglietti

  DOI：10.1016/j.ejmech.2008.07.025

  日期：2009.4

  A series of novel 5,7-diamino-3-phenyl-2-benzylamino, 2-phenoxy, and 2-thiophenyl substituted quinoxalines has been designed, synthesized and evaluated for their in vitro antitumor activity towards cell lines of nine different types of human cancers. Some of these compounds exhibited inhibitory effects on the growth of a wide range of cancer cell lines generally at 10(-6) M, in some cases at 10(-7) M and 10(-8) M concentrations. Within this series the benzylamino quinoxaline derivatives 1b-7b were the most active, whereas compound 2c showed the highest MG_MD value (-5.66). (C) 2008 Elsevier Masson SAS. All rights reserved.
• Pyridopyrimidines. 12. Synthesis of 8-deaza analogs of aminopterin and folic acid
  作者：Ananthachari Srinivasan、Arthur D. Broom

  DOI：10.1021/jo00322a004

  日期：1981.4
• SRINIVASAN A.; BROOM A. D., J. ORG. CHEM., 1980, 45, NO 19, 3746-3748
  作者：SRINIVASAN A.、 BROOM A. D.

  DOI：——

  日期：——