(R)-3-(tert-butoxycarbonylamino)pyrrolidine-2,5-dione

• 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: (R)-3-(tert-butoxycarbonylamino)pyrrolidine-2,5-dione
• 英文别名: tert-butyl (R)-(2,5-dioxopyrrolidin-3-yl)carbamate；tert-butyl N-(2,5-dioxopyrrolidin-3-yl)carbamate；3-(N-tBoc-D-amino)succinimide；(R)-tert-Butyl (2,5-dioxopyrrolidin-3-yl)carbamate；tert-butyl N-[(3R)-2,5-dioxopyrrolidin-3-yl]carbamate
• 化学式: C₉H₁₄N₂O₄
• 分子量: 214.221
• InChiKey: ADNLCKRUARJETQ-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-(tert-butoxycarbonylamino)pyrrolidine-2,5-dione 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-aminopyrrolidine-2,5-dione
  参考文献：
  名称：

  一种头孢吡普酯中间体（R）-1-叔丁氧基羰基-3-氨基吡咯烷的制备方法

  摘要：

  本发明公开了一种(R)‑1‑叔丁氧基羰基‑3‑氨基吡咯烷的制备方法，包括以下步骤：将D)天冬酰胺与氯化亚砜/甲醇反应生成D‑天冬酰胺甲基酯盐酸盐，接着用二碳酸二叔丁酯保护D‑天冬氨酸甲基酯盐酸盐的氨基，然后用氢化钠闭环，接着用TFA脱去3位氨基的BOC酸酐保护，再用硼氢化钠还原2，5位的二酮，最后用二碳酸二叔丁酯保护1位亚氨基得到(R)‑1‑叔丁氧基羰基‑3‑氨基吡咯烷黄色油状物。本发明成本低，污染小，易操作，有利于工业化生产，且产品纯度可达98％，为后续的高纯度头孢吡普的合成提供了保证。

  公开号：

  CN111592480B
• 作为产物：
  描述：

  Boc-D-天冬酰胺 在 N-羟基丁二酰亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (R)-3-(tert-butoxycarbonylamino)pyrrolidine-2,5-dione
  参考文献：
  名称：

  Synthesis of New Hydantoins Bearing Glutarimide or Succinimide Moiety and Their Evaluation for Cell Differentiation-inducing and Anti-angiogenic Activities

  摘要：

  Several derivatives of hydantoin containing glutarimide or succinimide at the 3-position were synthesized. The new hydantoin derivatives had a structure similar to that of thalidomide, and so may possess activity similar to that of thalidomide and/or its analogs, such as effects on cell differentiation and angiogenesis. Some hydantoins showed enhancing effects on all-trans retinoic acid (ATRA)-induced cell differentiation of human leukemia cell line HL-60 and anti-angiogenic activity on human umbilical vein endothelial cells (HUVEC). These new hydantoin derivatives were more effective than thalidomide in cell differentiation-inducing activity on HL-60 and anti-angiogenic activity on HUVEC.

  DOI：

  10.3987/com-15-13184

文献信息

• 一种头孢吡普酯中间体（R）-1-叔丁氧基羰基-3-氨基吡咯烷的制备方法
  申请人：山西千岫制药有限公司

  公开号：CN111592480B

  公开（公告）日：2023-06-23

  本发明公开了一种(R)‑1‑叔丁氧基羰基‑3‑氨基吡咯烷的制备方法，包括以下步骤：将D)天冬酰胺与氯化亚砜/甲醇反应生成D‑天冬酰胺甲基酯盐酸盐，接着用二碳酸二叔丁酯保护D‑天冬氨酸甲基酯盐酸盐的氨基，然后用氢化钠闭环，接着用TFA脱去3位氨基的BOC酸酐保护，再用硼氢化钠还原2，5位的二酮，最后用二碳酸二叔丁酯保护1位亚氨基得到(R)‑1‑叔丁氧基羰基‑3‑氨基吡咯烷黄色油状物。本发明成本低，污染小，易操作，有利于工业化生产，且产品纯度可达98％，为后续的高纯度头孢吡普的合成提供了保证。
• Small molecules against cereblon to enhance effector t cell function
  申请人：H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.

  公开号：US11395820B2

  公开（公告）日：2022-07-26

  Disclosed are small molecules against cereblon to enhance effector T cell function. Methods of making these molecules and methods of using them to treat various disease states are also disclosed.

  所公开的是抗脑龙的小分子，可增强效应 T 细胞的功能。还公开了制造这些分子的方法以及用它们治疗各种疾病的方法。
• SMALL MOLECULES AGAINST CEREBLON TO ENHANCE EFFECTOR T CELL FUNCTION
  申请人：H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.

  公开号：US20210177825A1

  公开（公告）日：2021-06-17

  Disclosed are small molecules against cereblon to enhance effector T cell function. Methods of making these molecules and methods of using them to treat various disease states are also disclosed.
• Synthesis of New Hydantoins Bearing Glutarimide or Succinimide Moiety and Their Evaluation for Cell Differentiation-inducing and Anti-angiogenic Activities
  作者：Jun-ichi Yamaguchi、Tomomi Noguchi-Yachide、Yuka Sakaguchi、Chiaki Shibata、Shinnosuke Kanuma、Akiko Yoshizaki、Yuka Takizawa、Yuichi Hashimoto

  DOI：10.3987/com-15-13184

  日期：——

  Several derivatives of hydantoin containing glutarimide or succinimide at the 3-position were synthesized. The new hydantoin derivatives had a structure similar to that of thalidomide, and so may possess activity similar to that of thalidomide and/or its analogs, such as effects on cell differentiation and angiogenesis. Some hydantoins showed enhancing effects on all-trans retinoic acid (ATRA)-induced cell differentiation of human leukemia cell line HL-60 and anti-angiogenic activity on human umbilical vein endothelial cells (HUVEC). These new hydantoin derivatives were more effective than thalidomide in cell differentiation-inducing activity on HL-60 and anti-angiogenic activity on HUVEC.
• Antibody-Catalyzed Rearrangement of a Peptide Bond: Mechanistic and Kinetic Investigations
  作者：Louis J. Liotta、Richard A. Gibbs、Scott D. Taylor、Patricia A. Benkovic、Stephen J. Benkovic

  DOI：10.1021/ja00122a001

  日期：1995.5

  Catalysis of the deamidation of asparagine residues may provide a powerful method for the deactivation of proteins. Catalytic antibodies (Gibbs et al. Science 1992, 258, 803) have been induced that catalyze the deamidation of a model dipeptide through an intermediate succinimide. Investigations of the mechanistic characteristics of two such antibodies, RG2-23C7 and RG2-2E4, revealed their ability to accelerate the hydrolysis of either the R- or S-enantiomers of the succinimide by factors of 10-500-fold to yield differing ratios of the aspartate and isoaspartate products. The mixed product ratios imply that two tetrahedral binding sites of unequal effectiveness were induced in response to the tetrahedral mimics (a phosphinate or secondary hydroxyl) within the hapten structure. The antibody RG2-2E4 also catalyzes the deamidation of either the D- or L-asparagine within the dipeptide through the intermediate cyclic imide, resulting in a multistep reaction sequence featuring a series of tetrahedral transition states. pH-rate profiles do not implicate functional groups within the antibodies' combining sites for either the deamidation or hydrolytic reactions. The strategy of bifunctional or higher order transition state mimics should provide a route to developing catalytic antibodies for reactions requiring multistep processing.