(3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)methyl nicotinate | 1246252-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)methyl nicotinate
• 英文别名: [3-(1,3-Dioxoisoindol-2-yl)-2,6-dioxopiperidin-1-yl]methyl pyridine-3-carboxylate
• CAS: 1246252-93-6
• 化学式: C₂₀H₁₅N₃O₆
• 分子量: 393.356
• InChiKey: DVFBXFLNHCVWDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)methyl nicotinate 在 盐酸 作用下， 以 水 为溶剂， 生成 [3-(1,3-Dioxoisoindol-2-yl)-2,6-dioxopiperidin-1-yl]methyl pyridine-3-carboxylate;hydrochloride
  参考文献：
  名称：

  Stable and orally bio-available pro-drugs of CPS11

  摘要：

  Stable and orally bio-available pro-drugs of CPS11 were synthesized. They are active on human umbilical vein endothelial cell proliferation assay and tube formation assay. The therapeutic efficacy and safety of 4 as a single agent or combined with Taxol in the treatment of MX-1 human breast cancer xenograft were evaluated. Compound 4 as a single agent failed to produce an anti-tumor activity, while it significantly enhanced antitumor potency of Taxol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.026
• 作为产物：
  描述：

  沙利度胺 在 水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)methyl nicotinate
  参考文献：
  名称：

  Stable and orally bio-available pro-drugs of CPS11

  摘要：

  Stable and orally bio-available pro-drugs of CPS11 were synthesized. They are active on human umbilical vein endothelial cell proliferation assay and tube formation assay. The therapeutic efficacy and safety of 4 as a single agent or combined with Taxol in the treatment of MX-1 human breast cancer xenograft were evaluated. Compound 4 as a single agent failed to produce an anti-tumor activity, while it significantly enhanced antitumor potency of Taxol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.026

文献信息

• Synthesis and Evaluation of Thalidomide and Phthalimide Esters as Antitumor Agents
  作者：Magdy A. H. Zahran、Yasmin G. Abdin、Amany M. A. Osman、Amira M. Gamal-Eldeen、Roba M. Talaat、Erik B. Pedersen

  DOI：10.1002/ardp.201400073

  日期：2014.9

  A series of thalidomide and phthalimide ester analogs were efficiently synthesized from N‐chloromethylthalidomide, N‐chloromethylphthalimide, and N‐(2‐bromoethyl)phthalimide derivatives with various biologically important carboxylic acids. The synthesized compounds were purified and characterized by various chromatographic and spectroscopic techniques. The antitumor activity of all the synthesized

  一系列沙利度胺和邻苯二甲酰亚胺酯类似物由 N-氯甲基沙利度胺、N-氯甲基邻苯二甲酰亚胺和 N-（2-溴乙基）邻苯二甲酰亚胺衍生物与各种重要的生物学羧酸有效合成。合成的化合物通过各种色谱和光谱技术进行纯化和表征。所有合成化合物对人肝癌和乳腺癌细胞的抗肿瘤活性都进行了筛选，结果表明邻苯二甲酰亚胺酯 6a 是对 MCF7 细胞毒性最好的化合物，而所有测试化合物对 HepG2 细胞均表现出非细胞毒性作用。化合物5a、6a和7a具有免疫抑制作用，而化合物5c、5d、6c、6d、7c和7d显示免疫刺激作用。同时，
• WATER-SOLUBLE THALIDOMIDE DERIVATIVES
  申请人：ZHANG Hesheng

  公开号：US20100240651A1

  公开（公告）日：2010-09-23

  A compound of formula (I), wherein R 1 represents H, or a C 1-4 alkyl group; R 2 represents H, a C 1-4 alkyl group, C(O)CHR 4 NR 5 R 6 , or C(O)W; or R 1 and R 2 taken together represent 1,3-propylene; R 3 represents H, a C 1-4 alkyl group, C(O)CHR 4 NR 5 R 6 , or C(O)W; or R 2 and R 3 taken together represent 1,3-propylene, 1,4-butylene, 1,5-pentylene, 1,6-hexylene, CH 2 OCH 2 , CH 2 SCH 2 or CH 2 NR 7 CH 2 , wherein R 7 represents H or a C 1-4 alkyl group; and when one of R 2 and R 3 represents H, or a C 1-4 alkyl group, the other one does not represent H; and R 8 represents H, or a C 1-4 alkyl group.

  化合物的化学式为（I），其中R1代表H或C1-4烷基；R2代表H，C1-4烷基，C（O）CHR4NR5R6或C（O）W；或R1和R2一起代表1,3-丙二基；R3代表H，C1-4烷基，C（O）CHR4NR5R6或C（O）W；或R2和R3一起代表1,3-丙二基，1,4-丁二基，1,5-戊二基，1,6-己二基，CH2OCH2，CH2SCH2或CH2NR7CH2，其中R7代表H或C1-4烷基；当R2和R3中的一个代表H或C1-4烷基时，另一个不代表H；R8代表H或C1-4烷基。