diethyl N-(p-aminobenzoyl)-glutamate | 13726-52-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酸类衍生物
• 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 N-(p-aminobenzoyl)-glutamate
• 英文别名: diethyl p-aminobenzoylglutamate；N-(4-amino-benzoyl)-glutamic acid diethyl ester；diethyl N-(4-aminobenzoyl)glutamate；N-<4-Amino-benzoyl>-dl-glutaminsaeure-diaethylester；N-<4-Amino-benzoyl>-glutaminsaeure-diaethylester；N--glutaminsaeure-diethylester；Diethyl 2-[(4-aminobenzoyl)amino]pentanedioate
• CAS: 13726-52-8；34136-22-6
• 化学式: C₁₆H₂₂N₂O₅
• 分子量: 322.361
• InChiKey: RJXFBLRRPYBPTM-UHFFFAOYSA-N

物化性质

• 熔点：
  139-142 °C(lit.)
• 沸点：
  460.98°C (rough estimate)
• 密度：
  1.1446 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  108
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  diethyl N-(p-aminobenzoyl)-glutamate 在 盐酸 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三氯化铝 、 sodium cyanoborohydride 、 碳酸氢钠 、 溶剂黄146 、 苯甲醚 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 64.0h， 生成 N5,N10-methylene-5,6,7,8-tetrahydro-8-deaza-8-thiafolic acid
  参考文献：
  名称：

  First Synthesis of 5,6,7,8-Tetrahydro-8-deaza-8-thiafolic Acid.

  摘要：

  5, 6, 7, 8-四氢-8-去氮-8-硫叶酸（3）作为比分异构混合物，通过将5-羟基异胞苷（6）与二乙基N-[p-(2-氨基-3-硫代丙基)氨基苯甲酰]谷氨酸（10）在6的C(6)位置经过N-溴丁酰亚胺/乙醇激活后进行热缩合合成。相应的N5, N10-亚甲基衍生物（5）在与甲醛反应后也被制备出来。

  DOI：

  10.1248/cpb.40.49
• 作为产物：
  描述：

  diethyl 2-aminopentanedioate 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 生成 diethyl N-(p-aminobenzoyl)-glutamate
  参考文献：
  名称：

  潜在的源自1,2-环氧茚满的抗肿瘤药

  摘要：

  许多胺和氨基酸衍生物与1,2-环氧茚满的反应提供了1-取代的氨基-2-茚满醇。尚未完成的初步测试未证明化合物具有明显的抗肿瘤活性。

  DOI：

  10.1002/jps.2600531118

文献信息

• Anti-cancer quinazoline derivatives
  申请人：National Research Development Corporation

  公开号：US05236927A1

  公开（公告）日：1993-08-17

  A compound of formula I: ##STR1## wherein R is hydrogen; oran alkyl, alkenyl or alkynyl group of up to 6 carbon atoms; nis O; 1 or 2; Z represents --CH.dbd.CH-- or --S--; each X independently represents halogeno, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or trifluoromethyl; and Y represents a group of formula: ##STR2## or a pharmaceutically acceptable salt or ester thereof.

  化合物I的化学式为：##STR1## 其中R为氢；或具有最多6个碳原子的烷基、烯基或炔基；n为O；1或2；Z代表--CH.dbd.CH--或--S--；每个X独立地代表卤素、C.sub.1-C.sub.4烷基、C.sub.1-C.sub.4烷氧基、硝基或三氟甲基；Y代表以下式的基团：##STR2## 或其药学上可接受的盐或酯。
• Compounds and methods for the detection of methotrexate
  申请人：Defined Diagnostics, LLC

  公开号：US11054430B2

  公开（公告）日：2021-07-06

  The disclosure relates generally to methods of detecting and quantifying methotrexate (MTX) in a sample. The methods disclosed herein decrease cross-reactivity and improve sensitivity of the detection.

  本公开内容一般涉及检测和量化样品中甲氨蝶呤（MTX）的方法。本文公开的方法可降低交叉反应，提高检测灵敏度。
• Varma,R.S.; Kapoor,A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1978, vol. 16, p. 325 - 326
  作者：Varma,R.S.、Kapoor,A.

  DOI：——

  日期：——
• Amide derivatives of ethacrynic acid: Synthesis and evaluation as antagonists of Wnt/β-catenin signaling and CLL cell survival
  作者：Guangyi Jin、Desheng Lu、Shiyin Yao、Christina C.N. Wu、Jerry X. Liu、Dennis A. Carson、Howard B. Cottam

  DOI：10.1016/j.bmcl.2008.12.067

  日期：2009.2

  A series of amides of ethacrynic acid was prepared and evaluated for their ability to inhibit Wnt signaling and decrease the survival of CLL cells. Several of the most potent derivatives were active in the low micromolar range. Reduction of the alpha,beta-unsaturated carbon-carbon double bond of EA abrogated both the inhibition of Wnt signaling as well as the decrease in CLL survival. Preliminary mechanism of action studies suggest that these derivatives covalently modify sulfhydryl groups present on transcription factors important for Wnt/beta-catenin signaling. (c) 2008 Elsevier Ltd. All rights reserved.
• Quinoxaline chemistry. Part 15. 4-[2-Quinoxalylmethylenimino]-benzoylglutamates and -benzoates, 4-[2-quinoxalylmethyl-N-methylamino]-benzoylglutamates as analogues of classical antifolate agents. Synthesis, elucidation of structures and in vitro evaluation of antifolate and anticancer activities
  作者：Mario Loriga、Sandra Piras、Giuseppe Paglietti、Maria Paola Costi、Alberto Venturelli

  DOI：10.1016/s0014-827x(02)00005-8

  日期：2003.1

  We report on an extension of our previous discovery of in vitro anticancer activity of trifluoromethylquinoxalines as analogues of classical and non-classical antifolic methotrexate and trimetrexate. In this case a small number of Schiff bases were obtained from the reaction of 2-bromethyl-3-R-6(7)trifluoromethylquinoxaline and ethyl p-aminobenzoylglutamate, ethyl p-aminobenzoate, p-toluidine instead of the expected 4-[2-quinoxalyl]methyl-N-methylanilino derivatives, which in turn formed with N-methylanilino derivatives. The reaction mechanism has been put forward. Structure elucidation of both Schiff bases and N-methylanilino analogues was achieved by a combination of 1H and 13C NMR spectra and hetcor experiments. Compounds 3a, 3b, 3c, 8, 11, 12, 13, Ie were tested in antifolic enzyme assay [Lactobacillus casei (LcTS), Leishmania major (LmTs), human Thymidylate synthase (hTs), human TS, human dihydrofolate reductase (hDHFR)] while compounds 3a, 3b, 3c were tested for anticancer activity. These results seem to indicate that the Schiff bases are somewhat active either as anticancer or as folate inhibitors, while compound Ie was selectively active against hDHFR with an inhibition constant (Ki) of 200 nM with a specificity of about 1000-folds with respect to hTS.