Diethyl 4-hydroxy-benzoyl-L-glutamate | 57963-63-0

• 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: Diethyl 4-hydroxy-benzoyl-L-glutamate
• 英文别名: 1,5-Diethyl N-(4-hydroxybenzoyl)-L-glutamate；diethyl (2S)-2-[(4-hydroxybenzoyl)amino]pentanedioate
• CAS: 57963-63-0
• 化学式: C₁₆H₂₁NO₆
• 分子量: 323.346
• InChiKey: QFXWYXFNNKEAHM-ZDUSSCGKSA-N

物化性质

• 沸点：
  517.6±50.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Diethyl 4-hydroxy-benzoyl-L-glutamate 在 sodium hydroxide 、 cesium bicarbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (S)-2-[4-(Pyrrolo[1,2-a]quinoxalin-4-ylmethoxy)-benzoylamino]-pentanedioic acid
  参考文献：
  名称：

  Quinoxaline chemistry. Part 16. 4-Substituted anilino and 4-substituted phenoxymethyl pyrrolo[1,2-a]quinoxalines and N-[4-(pyrrolo[1,2-a]quinoxalin-4-yl)amino and hydroxymethyl]benzoyl glutamates. Synthesis and evaluation of in vitro biological activity

  摘要：

  Twenty eight pyrrolo[1,2-a]quinoxalines bearing at position 4 various substituents related to the moieties present in classical and non classical antifolic agents were prepared and evaluated in vitro for antiproliferative activity. In an in vitro screening performed at NCI, several compounds emerged as potent antiproliferative agents at concentrations ranging between 10 and 100 microM. Interestingly, some of these compounds proved active also against bovine and murine DHFR (Farmaco 53 (1998) 480). More recently, a compound of classical antifolate type has been reported to be a potent inhibitor of hDHFR in vitro (Farmaco 58 (2003) 51). We then synthesized new derivatives that, in our hands, were endowed with in vitro antiproliferative activities as low as 3.4 microM against a panel of cell lines derived from hematological and solid tumours. In addition, a complete screening of cytotoxicity, antiretroviral HIV-1 and antimicrobial activity has been carried out.

  DOI：

  10.1016/s0014-827x(03)00101-0
• 作为产物：
  描述：

  4-acetoxybenzoyl chloride 在 乙醇 、 三乙胺 作用下， 生成 Diethyl 4-hydroxy-benzoyl-L-glutamate
  参考文献：
  名称：

  Oxygen Analogs of Pteroic Acid

  摘要：

  DOI：

  10.1021/ja01632a012

文献信息

• Quinoxaline chemistry
  作者：Gabriella Vitale、Paola Corona、Mario Loriga、Giuseppe Paglietti

  DOI：10.1016/s0014-827x(98)00075-5

  日期：1998.8

  Thirty quinoxalines bearing a substituted phenoxy or hydroxybenzoylglutamate group on position 2, a carboethoxy or carboxy group on position 3 and a trifluoromethyl group on position 6 or 7 of the heterocycle were prepared in order to evaluate the in vitro anticancer activity. Screening over 21 compounds selected at the National Cancer Institute (Bethesda, MD) showed that only few derivatives exhibited a moderate growth inhibition activity on various tumor panel cell lines at 10(-4) molar concentration. The acid derivatives showed no growth inhibition activity. The results obtained in this series seem to indicate that in general carboxy or carboethoxy groups close to O-link with phenyl or benzoyl glutamates on position 2 are detrimental for anticancer activity. (C) 1998 Elsevier Science S.A. All rights reserved.
• Quinoxaline chemistry. Part 11. 3-Phenyl-2 [phenoxy- and phenoxymethyl]-6(7) or 6,8-substituted quinoxalines and N-[4-(6(7)-substituted or 6,8-disubstituted-3-phenylquinoxalin-2-yl)hydroxy or hydroxymethyl]benzoylglutamates. Synthesis and evaluation of in vitro anticancer activity and enzymatic inhibitory activity against dihydrofolate reductase and thymidylate synthase
  作者：Paola Corona、Gabriella Vitale、Mario Loriga、Giuseppe Paglietti、Maria Paola Costi

  DOI：10.1016/s0014-827x(98)00054-8

  日期：1998.7

  Twenty-four out of twenty-nine quinoxalines were selected at the National Cancer Institute, Bethesda, Md, USA, for in vitro anticancer screening. Among these, 10 derivatives exhibited high values of percent tumor growth inhibition at a concentration of 10(-4) M in all cancer cell lines. Four of these compounds maintained these values at 10(-5) M, whereas a certain number exhibited significant values of percent inhibition at the most diluted concentrations (10(-8)-10(-6) M). Inhibitory activity against dihydrofolate reductase (DHFR) (bovine and rat liver) was determined for the most active compounds. This test showed that this type of quinoxaline exhibited an appreciable activity in comparison with the previously described aza analogues. In the other test (Lactobacillus casei, thymidylate synthase (TS), human HTS) no or poor activity was detected in both series of compounds. (C) 1998 Elsevier Science S.A. All rights reserved.
• Quinoxaline chemistry Part 10. Quinoxaline 10-oxa-analogues of trimetrexate (TMQ ) and of 5,8-dideazafolic acid. Synthesis and evaluation of in vitro anticancer activity
  作者：Gabriella Vitale、Paola Corona、Mario Loriga、Giuseppe Paglietti

  DOI：10.1016/s0014-827x(98)00003-2

  日期：1998.2

  Among twenty-eight novel compounds (twenty-two 2,13-disubstituted-6-[(substituted-phenoxy)methyl-quinoxalines and six 4-[(2,3-disubstituted-quinoxalin-6-yl) methoxy]benzoylglutamates) only thirteen were selected at NCI for evaluation of their in vitro anticancer activity. The results have shown that compounds 3l,c,b,e and 4b were endowed with Significantly high values of percent tumor growth inhibition on several tumor cell lines at 10(-4) M, while compound 3t was characterized by a high selectivity, being still strongly inhibiting on three cell lines at 10(-5) M. Comparison of the presently observed activity with that of the previously described aza-analogues confirms that the effected isosteric substitution is highly valuable in some cases. (C) 1998 Elsevier Science S.A. 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
• US4077957A
  申请人：——

  公开号：US4077957A

  公开（公告）日：1978-03-07