methyl 1,3-dioxo-2-phenylisoindoline-5-carboxylate | 64972-07-2

• 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: methyl 1,3-dioxo-2-phenylisoindoline-5-carboxylate
• 英文别名: methyl 2,3-dihydro-1,3-dioxo-2-phenyl-1H-isoindole-5-carboxylic acid；N-Phenyl-3-methoxycarbonyl-phthalimid；1,3-dioxo-2-phenyl-1,3-dihydro-isoindole-5-carboxylic acid methyl ester；N-phenyl-4-carbomethoxyphthalimide；methyl 1,3-dioxo-2-phenylisoindole-5-carboxylate
• CAS: 64972-07-2
• 化学式: C₁₆H₁₁NO₄
• 分子量: 281.268
• InChiKey: HCCMKPYOWKZBAL-UHFFFAOYSA-N

物化性质

• 熔点：
  204.5-206 °C(Solv: chloroform (67-66-3))
• 沸点：
  472.1±47.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-二氢-1,3-二氧代异苯并呋喃-5-羧酸甲酯 、 苯胺 在 sodium acetate 、 溶剂黄146 作用下， 反应 6.0h， 以94%的产率得到methyl 1,3-dioxo-2-phenylisoindoline-5-carboxylate
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of sulfonamides and carboxylates incorporating trimellitimides: Dual cyclooxygenase/carbonic anhydrase inhibitory actions

  摘要：

  Trimellitimides 6-21 were prepared and investigated in vivo for anti-inflammatory and ulcerogenic effects and in vitro for cytotoxicity. They were subjected to in vitro cyclooxygenase (COX-1/2) and carbonic anhydrase inhibition protocols. Compounds 6-11 and 18 exhibited anti-inflammatory activities and had median effective doses (ED50) of 34.3-49.8 mg kg(-1) and 63.6-86.6% edema inhibition relative to the reference drug celecoxib (ED50 : 33.9 mg kg(-1) and 85.2% edema inhibition). Compounds 6-11 and 18 were weakly cytotoxic at 10 mu M against 59 cell lines compared with the reference standard 5-fluorouracil (5-FU). Compounds 6-11 had optimal selectivity against COX-2. The selectivity index (SI) range was > 200-490 and was comparable to that for celecoxib [COX-2 (SI) > 416.7]. In contrast, compounds 12, 13, and 16-18 were nonselective COX inhibitors with a selectivity index range of 0.92-0.25. The carbonic anhydrase inhibition assay showed that sulfonamide incorporating trimellitimides 6-11 inhibited the cytosolic isoforms hCA I and hCA II, and tumor-associated isoform hCA IX. They were relatively more susceptible to inhibition by compounds 8, 9, and 11. The K-1 ranges were 54.1-81.9 nM for hCA I, 25.9-55.1 nM for hCA II, and 46.0-348.3 nM for hCA IX. (C) 2018 Elsevier Science. All rights reserved.

  DOI：

  10.1016/j.bioorg.2018.11.033

文献信息

• Investigation of the inhibitory effects of isoindoline-1,3-dion derivatives on hCA-I and hCA-II enzyme activities
  作者：Hayrunnisa Nadaroglu、Azize Alaylı Gungor、Özlem Gundogdu、Nurhan Horasan Kishali、Belgin Sever、Mehlika Dilek Altintop

  DOI：10.1016/j.molstruc.2019.07.070

  日期：2019.12

  out for all compounds and acetazolamide (AAZ), the reference agent, in the active sites of hCA I and hCA II. Generally, the compounds showed high affinity through salt bridge formation and metal coordination with Zn2+ ion and π-stacking interaction with His94 residue. According to in silico Absorption, Distribution, Metabolism and Excretion (ADME) studies, the pharmacokinetic parameters of all compounds

  摘要 抑制碳酸酐酶 (CA) 已成为治疗青光眼、癫痫、肥胖和癌症等多种疾病的一种有前景的方法。因此，CA抑制剂（CAIs）的设计是药物化学的一个突出领域。由于异吲哚啉-1,3-二酮作为 CAI 的治疗潜力，本文使用亲和层析和一系列异二氢吲哚-1,3-二酮对水合酶活性的抑制作用从人红细胞中纯化 hCA I 和 hCA II 同工酶。研究了这些同工酶。在这些化合物中，发现化合物 3a 是对 hCA I 最有效的化合物，IC50 值为 7.02 μM，而化合物 3c 是对 hCA II 最有效的化合物，IC50 值为 6.39 μM。而且，在 hCA I 和 hCA II 的活性位点对所有化合物和乙酰唑胺 (AAZ)（参考药物）进行了分子对接研究。通常，这些化合物通过盐桥形成和与 Zn2+ 离子的金属配位以及与 His94 残基的 π 堆积相互作用表现出高亲和力。根据计算机吸收、分布、代谢和排泄
• Evaluation of xanthine oxidase inhibitor properties on isoindoline-1,3-dion derivatives and calculation of interaction mechanism
  作者：Özlem Gunduğdu、Samir Abbas Ali Noma、Tugba Taskin-Tok、Burhan Ateş、Nurhan Kishali

  DOI：10.1016/j.molstruc.2019.127523

  日期：2020.3

  the present study was to synthesis of isoindole-1,3(2H)-dione (Phthalimides) derivatives and to investigation the inhibition of xanthine oxidase (XO). In study, xanthine oxidase inhibitory activities of complexes were observed in the range from 7.15 to 22.56 μM for isoindole-1,3-dione (2a-c and 3a-c). N-phenyl isoindole-1,3-dione derivatives (2c, 3c) showed better activity (almost two times) than the

  摘要 本研究的目的是合成异吲哚-1,3(2H)-二酮(Phthalimides) 衍生物并研究黄嘌呤氧化酶(XO) 的抑制作用。在研究中，对于异吲哚-1,3-二酮（2a-c 和 3a-c），观察到复合物的黄嘌呤氧化酶抑制活性范围为 7.15 至 22.56 μM。N-苯基异吲哚-1,3-二酮衍生物(2c, 3c)比其他两种衍生物(N-甲基(2a, 3a), N-乙基(2b, 3b))表现出更好的活性(几乎是两倍)。这意味着苯环 (R) 显着增强了配合物的黄嘌呤氧化酶抑制作用。同时，还通过提供抑制效率和估计异吲哚-1,3-dion 衍生物的相互作用机制，研究了这些化合物对 XO 的分子对接研究与 XO。
• PHOTOCONDUCTORS CONTAINING TRIMELLITIMIDE ESTERS
  申请人：Weiss David S.

  公开号：US20090087762A1

  公开（公告）日：2009-04-02

  The present invention is an electrophotographic photoconductor having a photosensitive layer on a conductive substrate. The photosensitive layer contains trimellitimide esters additives.

  本发明是一种在导电基板上具有感光层的电子照相感光体。感光层含有三嗪酸酐酯添加剂。
• Photoconductors containing trimellitimide esters
  申请人：Eastman Kodak Company

  公开号：US07923184B2

  公开（公告）日：2011-04-12

  The present invention is an electrophotographic photoconductor having a photosensitive layer on a conductive substrate. The photosensitive layer contains trimellitimide esters additives.

  本发明是一种电子照相感光鼓，其具有在导电基底上的感光层。感光层包含三苯基甲酸酯添加剂。
• SHUSHERINA N. P.; LAPTEVA V. L.; XRUSHCHEVA O. V., ZH. ORGAN. XIMII, 1977, 13, HO 9, 1930-1933
  作者：SHUSHERINA N. P.、 LAPTEVA V. L.、 XRUSHCHEVA O. V.

  DOI：——

  日期：——