2-[2-(吗啉-4-磺酰基)乙基]-2,3-二氢-1H-异吲哚-1,3-二酮 | 173336-67-9

• 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
• 中文名称: 2-[2-(吗啉-4-磺酰基)乙基]-2,3-二氢-1H-异吲哚-1,3-二酮
• 英文名称: 2-(2-(morpholinosulfonyl)ethyl)isoindoline-1,3-dione
• 英文别名: 2-(2-(morpholinosulfonyl)ethyl)isoindole-1,3-dione；2-phthaloylaminoethyl-N-(morpholin-4-yl)-sulfonamide；2-[2-(morpholine-4-sulfonyl)ethyl]-2,3-dihydro-1H-isoindole-1,3-dione；2-(2-morpholin-4-ylsulfonylethyl)isoindole-1,3-dione
• CAS: 173336-67-9
• 化学式: C₁₄H₁₆N₂O₅S
• 分子量: 324.357
• InChiKey: IVEIQOGSYKUHEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[2-(吗啉-4-磺酰基)乙基]-2,3-二氢-1H-异吲哚-1,3-二酮 在 sodium hydroxide 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 生成 (2S,4S)-4-Mercapto-2-[2-(morpholine-4-sulfonyl)-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester
  参考文献：
  名称：

  Synthesis and biological properties of new 1β-methylcarbapenems

  摘要：

  The synthesis and biological activity of the novel series of 1 beta-methylcarbapenems, 1 and 2 were described. Most compounds displayed high potent antibacterial activity. The best compound in this series, 2a (IH201; R-2=NH2) showed an excellent and a broad spectrum as well as high renal DHP-I stability. It also possessed good in vivo efficacy and high safety. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00270-4
• 作为产物：
  描述：

  1,3-二氢-1,3-二氧代-2H-异吲哚-2-乙烷磺酸 在 五氯化磷 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 2-[2-(吗啉-4-磺酰基)乙基]-2,3-二氢-1H-异吲哚-1,3-二酮
  参考文献：
  名称：

  Synthesis and biological properties of new 1β-methylcarbapenems

  摘要：

  The synthesis and biological activity of the novel series of 1 beta-methylcarbapenems, 1 and 2 were described. Most compounds displayed high potent antibacterial activity. The best compound in this series, 2a (IH201; R-2=NH2) showed an excellent and a broad spectrum as well as high renal DHP-I stability. It also possessed good in vivo efficacy and high safety. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00270-4

文献信息

• .delta.-amino-.gamma.-hydroxy-.omega.-aryl-alkanoic acid amides
  申请人：Ciba-Geigy Corporation

  公开号：US05559111A1

  公开（公告）日：1996-09-24

  .delta.-Amino-.gamma.-hydroxy-.omega.-aryl-alkanoic acid amides of formula I ##STR1## and the salts thereof, have renin-inhibiting properties and can be used as antihypertensive medicinal active ingredients.

  公式I的.delta.-氨基-.gamma.-羟基-.ω-芳基-烷基酸酰胺及其盐具有抑制肾素的性质，可用作降压药物活性成分。
• [EN] METHODS OF TREATING ALZHEIMER'S DISEASE USING ARYL ALKANOIC ACID AMIDES<br/>[FR] METHODES DE TRAITEMENT DE LA MALADIE D'ALZHEIMER PAR DES AMIDES D'ACIDE ARYL ALCANOIQUE
  申请人：ELAN PHARM INC

  公开号：WO2003103653A1

  公开（公告）日：2003-12-18

  Disclosed are methods for treating Alzheimer’s disease, and other diseases, and/or inhibiting beta-secretase enzyme, and/or inhibiting deposition of A beta peptide in a mammal, by use of compounds of formula 1 (1) wherein the variables R1-R8 and X are defined herein.

  揭示了一种治疗阿尔茨海默病和其他疾病，和/或抑制β-分泌酶，和/或通过使用式1（1）中定义的化合物在哺乳动物体内抑制Aβ肽的沉积的方法。其中变量R1-R8和X在此处定义。
• Quinazolines and related heterocyclic compounds and their therapeutic use
  申请人：Vereniging voor Christelijk Hoger Onderwijs, Wetenschappelijk Onderzoek en Patiëntenzorg

  公开号：EP2077263A1

  公开（公告）日：2009-07-08

  A compound of the formula wherein X is CR1 or N; Y is CR3 or N; R1, R3, R4, R5 and R6 are independently H, F, Cl, Br, I, or a hydrocarbon group which optionally contains one or more heteroatoms; R7 is a heterocyclic group including one or more N atoms; R' is Rx or NRyRz wherein Rx, Ry and Rz are each H or the same or different groups, including cyclic groups formed by Ry and Rz with the N atom, of up to 20 C atoms and optionally including up to 3 further heteroatoms selected from N, O and S; or a pharmaceutically acceptable salt, ester or solvate thereof, has therapeutic utility.

  该化合物的公式为X是CR1或N；Y是CR3或N；R1、R3、R4、R5和R6分别独立地为H、F、Cl、Br、I或一个可能含有一个或多个杂原子的碳氢基团；R7是一个包括一个或多个N原子的杂环基团；R'是Rx或NRyRz，其中Rx、Ry和Rz分别为H或相同或不同的基团，包括由Ry和Rz与N原子形成的环基团，最多包含20个碳原子，且可选地包含最多3个进一步从N、O和S中选择的杂原子；或其药用盐、酯或溶剂化合物具有治疗用途。
• Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- and N-substituted benzoyltaurinamide derivatives
  作者：Özlem AKGÜL、Mümin Alper ERDOĞAN、Derviş BİRİM、Çağla KAYABAŞI、Cumhur GÜNDÜZ、Güliz ARMAĞAN

  DOI：10.3906/kim-2009-1

  日期：——

  In this study, a group of 4-substituted benzoyltaurinamide derivatives were designed, synthesized, and investigated for their anticancer activity against three cancer cell lines and one nontumorigenic cell line by MTT assay. Among the final compounds, methoxyphenyl derivatives 14, 15, 16 were found to be effective against all the tested cancerous cell lines with promising selectivity. The most active compounds were further evaluated to determine the molecular mechanism of their anticancer activity by using western blot assay and the Annexin V-FITC/PI test. Compound 14 (in SH-SY5Y and MDA-MB-231 cell lines) and 15 (in SH-SY5Y cell line) were found to induce intrinsic apoptotic pathway by upregulating BAX, caspase-3, and caspase-9, while downregulating Bcl-2 and Bcl-xL expression levels. According to mechanistic studies, compounds displayed their anticancer activity via three different mechanisms: a. caspase-dependent, b. caspase-independent, and c. caspase-dependent pathway that excluded caspase-9 activation. As a result, this study provides interesting data which can be used to design new taurine-based anticancer derivatives.

  本研究设计、合成了一组 4-取代苯甲酰脲酰胺衍生物，并通过 MTT 试验研究了它们对三种癌细胞株和一种非致癌细胞株的抗癌活性。在最终化合物中，甲氧基苯基衍生物 14、15 和 16 对所有测试的癌细胞株都有效，并具有良好的选择性。为了确定其抗癌活性的分子机制，我们使用 Western 印迹分析法和 Annexin V-FITC/PI 测试法对最具活性的化合物进行了进一步评估。研究发现，化合物 14（在 SH-SY5Y 和 MDA-MB-231 细胞系中）和化合物 15（在 SH-SY5Y 细胞系中）通过上调 BAX、caspase-3 和 caspase-9，同时下调 Bcl-2 和 Bcl-xL 的表达水平，诱导细胞内在凋亡通路。根据机理研究，化合物通过三种不同的机制显示其抗癌活性：a. 依赖于 caspase 的途径；b. 不依赖于 caspase 的途径；c. caspase 依赖性途径，但不包括 caspase-9 激活。因此，这项研究提供了有趣的数据，可用于设计新的牛磺酸类抗癌衍生物。
• Quinazolines and related heterocyclic compounds, and their therapeutic use
  申请人：Smits Rogier Adriaan

  公开号：US08530486B2

  公开（公告）日：2013-09-10

  A compound of the formula (I) wherein X is CR1 or N; Y is CR3 or N; R1, R3, R4, R5 and R6 are independently H, F, Cl, Br, I, or a hydrocarbon group which optionally contains one or more heteroatoms; R7 is a heterocyclic group including one or more N atoms; R′ is Rx or NRyRz wherein Rx, Ry and Rz are each H or the same or different groups, including cyclic groups formed by Ry and Rz with the N atom, of up to 20 C atoms and optionally including up to 3 further heteroatoms selected from N, O and S; or a pharmaceutically acceptable salt, ester or solvate thereof.

  化合物的公式（I），其中X是CR1或N; Y是CR3或N; R1、R3、R4、R5和R6独立地为H、F、Cl、Br、I或含有一个或多个杂原子的碳氢基团; R7是包括一个或多个N原子的杂环基团; R′是Rx或NRyRz，其中Rx、Ry和Rz分别为H或相同或不同的基团，包括由Ry和Rz与N原子形成的环状基团，长度最长可达20个C原子，并且可选地包括最多3个从N、O和S中选择的进一步杂原子; 或其药学上可接受的盐、酯或溶剂化物。