benzyl (2,5-dioxopyrrolidin-1-yl) glutarate | 104253-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (2,5-dioxopyrrolidin-1-yl) glutarate
• 英文别名: monobenzyl glutaryl N-hydroxysuccinimide；Pentanedioic acid benzyl ester 2,5-dioxo-pyrrolidin-1-yl ester；1-O-benzyl 5-O-(2,5-dioxopyrrolidin-1-yl) pentanedioate
• CAS: 104253-38-5
• 化学式: C₁₆H₁₇NO₆
• 分子量: 319.314
• InChiKey: NBSKLACMJQNRED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (2,5-dioxopyrrolidin-1-yl) glutarate 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-{(1S,2R)-2,3-Dihydroxy-1-[2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yl)-ethylcarbamoyl]-propylcarbamoyl}-butyric acid
  参考文献：
  名称：

  C-Fucopeptides as selectin antagonists: Attachment of lipid moieties enhances the activity

  摘要：

  The biological activity of a potent selectin antagonist could be 40-fold enhanced by attachment of a lipid moiety. Also an enantioselective synthesis of beta,omega-dihydroxyamino acids by Sharpless asymmetric dihydroxylation (AD-reaction) allowed general access to this important class of compounds. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02121-1
• 作为产物：
  描述：

  戊二酸酐 在 4-二甲氨基吡啶 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 生成 benzyl (2,5-dioxopyrrolidin-1-yl) glutarate
  参考文献：
  名称：

  唾液酸化的Lewis X模拟物的合成：以O - α-岩藻糖基-（1 R，2 R）-2-氨基环己醇为核心结构

  摘要：

  设计并制备了六种含有O - α-岩藻糖基- （1 R，2 R）-2-氨基环己醇的糖肽作为唾液酸化的Lewis X模拟物。与SLe X（IC 50 = 0.5 mM）相比，化合物2和6对E-选择素的结合亲和力更好，IC 50值分别为0.4和0.2 mM。

  DOI：

  10.1016/0040-4039(96)01114-8
• 作为试剂：
  描述：

  在 N,N-二异丙基乙胺 、 benzyl (2,5-dioxopyrrolidin-1-yl) glutarate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  WO2008/75192

  摘要：

  公开号：

文献信息

• Synthesis of Sialyl Lewis X Mimetics and Related Structures Using the Glycosyl Phosphite Methodology and Evaluation of E-Selectin Inhibition
  作者：Chun-Cheng Lin、Makoto Shimazaki、Marie-Pierre Heck、Shin Aoki、Ruo Wang、Teiji Kimura、Helena Ritzèn、Shuichi Takayama、Shih-Hsiung Wu、Gabriel Weitz-Schmidt、Chi-Huey Wong

  DOI：10.1021/ja952265x

  日期：1996.1.1

  reactivity and stereoselectivity, and the application of this methodology to the synthesis of Lewis X (Lex), Lewis Y (Ley), glycopeptides, and sialyl Lewis X (SLex) mimetics. Both α-O-fucosyl-l-threonine and α-O-fucosyl-(1R,2R)-2-aminocyclohexanol were found to be effective templates for the chemical/enzymatic synthesis of SLex mimetics, and some fucopeptides prepared were 5−10 times more active than SLex as

  本文描述了我们最近对用于糖基化反应的糖基亚磷酸酯的研究，特别强调了保护基团和立体化学对异头反应性和立体选择性的影响的研究，以及该方法在合成 Lewis X (Lex)、Lewis Y 中的应用(Ley)、糖肽和唾液酸路易斯 X (SLex) 模拟物。发现 α-O-岩藻糖基-l-苏氨酸和 α-O-岩藻糖基-(1R,2R)-2-氨基环己醇都是 SLex 模拟物化学/酶促合成的有效模板，制备的一些岩藻肽是 5-10作为 E-选择素抑制剂的活性比 SLex 高出数倍。
• GLUCOSE-RESPONSIVE INSULIN CONJUGATES
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20150105317A1

  公开（公告）日：2015-04-16

  Insulin conjugates comprising an insulin molecule covalently attached to at least one bi-dentate linker having two arms, each arm independently attached to a ligand comprising a saccharide and wherein the saccharide for at least one ligand of the linker is fucose are disclosed. The insulin conjugates display a pharmacokinetic (PK) and/or pharmacodynamic (PD) profile that is responsive to the systemic concentrations of a saccharide such as glucose or alpha-methylmannose even when administered to a subject in need thereof in the absence of an exogenous multivalent saccharide-binding molecule such as Con A.

  本发明涉及胰岛素共轭物，包括将胰岛素分子共价连接至至少一个双齿配体的连接物中，每个配体独立连接到包含一种含糖和其中至少一个连接物的配体的糖类，其中连接物的至少一个配体的糖类为岩藻糖。这些胰岛素共轭物展示出对系统浓度的糖类（如葡萄糖或α-甲基甘露糖）具有响应的药代动力学（PK）和/或药效动力学（PD）特性，即使在给予需要的受试者时，也不需要外源多价糖类结合分子（如Con A）。
• [EN] GLUCOSE-RESPONSIVE INSULIN CONJUGATES<br/>[FR] CONJUGUÉS D'INSULINE SENSIBLES AU GLUCOSE
  申请人：MERCK SHARP & DOHME

  公开号：WO2016164288A1

  公开（公告）日：2016-10-13

  Insulin conjugates comprising an insulin analog molecule covalently attached to at least one bi-dentate linker having two arms, each arm independently attached to a ligand comprising a saccharide and wherein the saccharide for at least one ligand of the linker is fucose are disclosed. The insulin conjugates display a pharmacokinetic (PK) and/or pharmacodynamic (PD) profile that is responsive to the systemic concentrations of a saccharide such as glucose or alpha-methylmannose even when administered to a subject in need thereof in the absence of an exogenous multivalent saccharide-binding molecule such as Con A.

  包含胰岛素类似物分子的胰岛素共轭物，与至少一个双齿配体连接物共价连接，每个配体独立连接到一个含有糖类的配体，并且连接物中至少一个配体的糖类是富马醇。这些胰岛素共轭物显示出对糖类（如葡萄糖或α-甲基甘露糖）的体内浓度响应的药代动力学（PK）和/或药效动力学（PD）特性，即使在向需要者施用时，也无需外源多价糖类结合分子（如Con A）。
• IP4-4,6 SUBSTITUTED DERIVATIVE COMPOUNDS
  申请人：Sanifit Therapeutics S.A.

  公开号：EP4036097A1

  公开（公告）日：2022-08-03

  The present invention provides IP4-4,6 substituted derivatives, their methods of synthesis and their uses. In some aspects, the IP4-4,6 derivative is a compound of formula I wherein R1, R3, R7, and R11 are OPO32-, and R5 and R9 are selected from the group consisting of -O(Alkyl)nX, -O(Alkyl)yCy(Alkyl2)y-Z, -O(Alkyl)yA(Alkyl)y-Z', and their thiophosphate analogs. Also provided are methods, pharmaceutical compositions and formulations, methods of use, articles of manufacture, and kits for the treatment of diseases and conditions such as pathological crystallization-related diseases and conditions.

  本发明提供了IP4-4,6取代衍生物，它们的合成方法和用途。在某些方面，IP4-4,6衍生物是化合物I的化合物，其中R1、R3、R7和R11是OPO32-，R5和R9是从-O（烷基）nX、-O（烷基）yCy（烷基2）y-Z、-O（烷基）yA（烷基）y-Z'及其硫代磷酸盐类中选择的。还提供了治疗病理结晶相关疾病和病症等疾病和病症的方法、制药组合物和配方、使用方法、制品和工具箱。
• A CONJUGATE OF A TUBULYSIN ANALOG WITH BRANCHED LINKERS
  申请人：Hangzhou DAC Biotech Co., Ltd.

  公开号：US20200276261A1

  公开（公告）日：2020-09-03

  The present invention relates to the conjugation of a tubulysin analog compound to a cell-binding molecule with branched/side-chain linkers for having better delivery of the conjugate compound and targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of a tubulysin analog molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and autoimmune disease.