5-(benzyloxy)-2-(((benzyloxy)carbonyl)amino)-5-oxopentanoic acid | 254980-13-7

• 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: 5-(benzyloxy)-2-(((benzyloxy)carbonyl)amino)-5-oxopentanoic acid
• 英文别名: 5-Oxo-5-phenylmethoxy-2-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 254980-13-7
• 化学式: C₂₀H₂₁NO₆
• 分子量: 371.39
• InChiKey: TWIVXHQQTRSWGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  5-(benzyloxy)-2-(((benzyloxy)carbonyl)amino)-5-oxopentanoic acid 在 sodium acetate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 生成 4-Benzyloxycarbonylamino-4-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butyric acid benzyl ester
  参考文献：
  名称：

  Synthesis of 3-amino-3-(5-fluorouracil-1-yl)propionic acid and 4-amino-4-(5-fluorouracil-1-yl)butyric acid derivatives.

  摘要：

  3-酰氨基-3-(5-氟尿嘧啶-1-基)丙酸酯 (3a, b) 和 4-酰氨基-4-(5-氟尿嘧啶-1-基)丁酸酯 (3c-e) 分别通过电化学氧化从3-酰氨基-3-羧基丙酸酯 (1a, b) 和4-酰氨基-4-羧基丁酸酯 (1c-e) 合成。对苄基酯 (3a, c, d) 的催化氢解反应生成相应的羧酸 (4a', c', d')，而未裂解邻位二胺基团。

  DOI：

  10.1248/cpb.28.1137

文献信息

• Design, synthesis and biological evaluation of glutamic acid derivatives as anti-oxidant and anti-inflammatory agents
  作者：Suvarna H. Pagire、Eunhye Lee、Haushabhau S. Pagire、Eun Jung Bae、Soo Jung Ryu、Dahye Lee、Min Hee Kim、Geum Ran Kim、Kyu-Seok Hwang、Sukyung Ahn、Jin Hee Maeng、Jin Sook Song、Myung Ae Bae、Don Hang Lee、Jin Hee Ahn

  DOI：10.1016/j.bmcl.2017.11.012

  日期：2018.2

  A series of glutamic acid derivatives was synthesized and evaluated for their antioxidant activity and stability. We found several potent and stable glutamic acid derivatives. Among them, compound 12b exhibited good in vitro activity, chemical stability and cytotoxicity. A prototype compound 12b showed an anti-inflammatory effect in LPS-stimulated RAW 264.7 cell lines and in a zebrafish model.

  合成了一系列谷氨酸衍生物，并评估了其抗氧化活性和稳定性。我们发现了几种有效且稳定的谷氨酸衍生物。其中，化合物12b显示出良好的体外活性，化学稳定性和细胞毒性。原型化合物12b在LPS刺激的RAW 264.7细胞系和斑马鱼模型中显示出抗炎作用。
• PRODRUGS OF CYTOTOXIC ACTIVE AGENTS HAVING ENZYMATICALLY CLEAVABLE GROUPS
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20190077752A1

  公开（公告）日：2019-03-14

  The invention relates to novel prodrugs or conjugates of the general formula (Ia) in which cytotoxic drugs, for example kinesin spindle protein inhibitors, are masked with legumain-cleavable groups and hence release the drug, and to the use of these prodrugs or conjugates for treatment and/or prevention of diseases, and to the use of these prodrugs or conjugates for production of medicaments for treatment and/or prevention of diseases, especially of hyperproliferative and/or angiogenic disorders, for example cancers.

  该发明涉及通式(Ia)的新型前药或结合物，其中细胞毒性药物，例如动力蛋白抑制剂，被腿蛋白酶可切割基团掩蔽，从而释放药物，并且涉及使用这些前药或结合物用于治疗和/或预防疾病，以及使用这些前药或结合物用于生产用于治疗和/或预防疾病的药物，特别是治疗和/或预防高增殖和/或血管生成异常的疾病，例如癌症。
• [EN] CHEMOTHERAPEUTIC AGENTS<br/>[FR] AGENTS CHIMIOTHÉRAPEUTIQUES
  申请人：BIOXINESS PHARMACEUTICALS INC

  公开号：WO2019169017A1

  公开（公告）日：2019-09-06

  This invention is directed to chemotherapeutic conjugates comprising a an amino acid mimetic and gemcitabine.

  本发明涉及一种化疗偶联物，包括一种氨基酸类似物和吉西他滨。
• Optically-active derivatives of (R) 5-pentylamino-5-oxopentanoic acid
  申请人：Rotta Research Laboratorium SpA

  公开号：US05130474A1

  公开（公告）日：1992-07-14

  There are described optically active derivatives (R) 5-pentylamino-5-oxopentanoic acid and their pharmaceutically acceptable salts, having antagonistic activity towards cholecystokinin, and with the formula: ##STR1## in which R.sub.1 is selected from the groups 2-naphthyl, 3,4-dichlorobenzoyl and 3,4-dimethylbenzoyl and R.sub.2 is a pentyl group or an alkoxyalkyl group with 4 carbon atoms, and in which the substituents on the central chiral group (marked with an asterisk in Formula (I)), have the R (rectus) conformation.

  描述了光学活性衍生物（R）5-戊基氨基-5-氧代戊酸及其药学上可接受的盐，具有对胆囊收缩素的拮抗活性，其化学式为：##STR1## 其中R.sub.1来自2-萘基，3,4-二氯苯甲酰基和3,4-二甲基苯甲酰基等基团，R.sub.2是戊基或具有4个碳原子的烷氧基烷基，且中央手性基团（在式（I）中用星号标记）的取代基具有R（直）构象。
• Derivatives of glutamic and aspartic acids, a method of preparing them,
  申请人：Rotta Research Laboratorium S.P.A.

  公开号：US05723494A1

  公开（公告）日：1998-03-03

  Compounds represented by general formula (I) and (II), in which r is 1 or 2, R.sub.2 and R.sub.3 are selected independently from H, CH.sub.3, C.sub.2 H.sub.5 and CHO, provided that R.sub.2 and R.sub.3 are not simultaneously CHO, and in which R.sub.1 is selected from: an aminoalkyl adamantyl group, a monocyclic aminoalkyl group, a dicyclic aminospiro group, a dicyclic amino group (orthofused), a dicyclic amino group, and azacycloalkyl group, an azadicyclic group (orthofused), a dicyclic azaspiro group, and azadicyclic group, and azacycloalkyl group, and a linear or branched aminoalkyl group.

  通式(I)和(II)所代表的化合物，其中r为1或2，R.sub.2和R.sub.3独立地选择自H、CH.sub.3、C.sub.2 H.sub.5和CHO，但要求R.sub.2和R.sub.3不能同时为CHO，而R.sub.1从以下选取：氨基烷基金刚烷基、单环氨基烷基、双环氨基螺环基、双环氨基基(正融合)、双环氨基基、氮杂环烷基、氮杂双环基(正融合)、双环氮杂螺环基、氮杂双环基和氮杂环烷基，以及线性或支链氨基烷基。