4-Carbomethoxy-N-methylphthalimide | 79431-06-4

• 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: 4-Carbomethoxy-N-methylphthalimide
• 英文别名: N-Methylmellitimide；methyl 2,3-dihydro-2-methyl-1,3-dioxo-1H-isoindole-5-carboxylate；Methyl 2-methyl-1,3-dioxoisoindoline-5-carboxylate；methyl 2-methyl-1,3-dioxoisoindole-5-carboxylate
• CAS: 79431-06-4
• 化学式: C₁₁H₉NO₄
• 分子量: 219.197
• InChiKey: QJXYRQZMVBPHIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  potassium propionate 、 4-Carbomethoxy-N-methylphthalimide 以 水 、 丙酮 为溶剂， 生成 3-ethyl-3-hydroxy-2-methyl-2,3-dihydro-1H-isoindol-5-carbonic acid methyl ester
  参考文献：
  名称：

  Griesbeck, Axel G.; Oelgemöller, Michael, Synlett, 1999, # 4, p. 492 - 494

  摘要：

  DOI：
• 作为产物：
  描述：

  偏苯三酸酐 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 42.0h， 生成 4-Carbomethoxy-N-methylphthalimide
  参考文献：
  名称：

  异吲哚啉-1,3-dion 衍生物对 hCA-I 和 hCA-II 酶活性抑制作用的研究

  摘要：

  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

  DOI：

  10.1016/j.molstruc.2019.07.070

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
• Nitrogen-containing 5-membered ring compound
  申请人：Yasuda Kosuke

  公开号：US20080153821A1

  公开（公告）日：2008-06-26

  The present invention is to provide an aliphatic nitrogen-containing 5-membered ring compound represented by the formula [I]: wherein symbols in the formula have the following meanings; A: —CH 2 — or —S—, B: CH or N, R 1 : H, a lower alkyl group, etc., X: a single bonding arm, —CO—, -Alk-CO—, —COCH 2 —, -Alk-O—, —O—CH 2 —, —SO 2 —, —S—, —COO—, —CON(R 3 )—, -Alk-CON(R 3 )—, —CON(R 3 )CH 2 —, —NHCH 2 —, etc., R 3 : hydrogen atom or a lower alkyl group, Alk: a lower alkylene group, and R 2 : (1) a cyclic group which may be substituted, (2) a substituted amino group, etc., provided that when X is —CO—, then B is N, or a pharmaceutically acceptable salt thereof.

  本发明提供一种由式[I]表示的脂肪族氮含有5元环化合物，其中式中符号的含义如下：A：—CH2—或—S—，B：CH或N，R1：H、低碳基等，X：一个单键臂、—CO—、-Alk-CO—、—COCH2—、-Alk-O—、—O—CH2—、—SO2—、—S—、—COO—、—CON(R3)—、-Alk-CON(R3)—、—CON(R3)CH2—、—NHCH2—等，R3：氢原子或低碳基，Alk：低碳亚烷基，以及R2：（1）一个可能被取代的环状基团，（2）一个取代的氨基团等，前提是当X为—CO—时，B为N，或其药学上可接受的盐。
• Photochemical additions of alkenes to phthalimides. Mechanistic investigations on the stereochemistry of alkene additions and the effect of aryl substituents on the regiochemistry of alkene additions
  作者：P. H. Mazzocchi、P. Wilson、F. Khachik、L. Klingler、S. Minamikawa

  DOI：10.1021/jo00166a009

  日期：1983.9
• Novel and Efficient Azomethine Ylide Forming Photoreactions of N-(Silylmethyl)phthalimides and Related Acid and Alcohol Derivatives
  作者：Ung Chan Yoon、Dong Uk Kim、Chan Woo Lee、Young Sun Choi、Yean-Jang Lee、Herman L. Ammon、Patrick S. Mariano

  DOI：10.1021/ja00115a004

  日期：1995.3

  An investigation of the photochemistry of N-(silylmethyl)phthalimides and related alpha-phthaloylacetic acids and 2-phenylethanol derivatives has uncovered new excited state processes resulting in the formation of azomethine ylide intermediates. Irradiation of N-[(trimethylsilyl)methyl]phthalimide in MeCN promotes C to O silyl transfer to generate the corresponding azomethine ylide which is efficiently trapped by reaction with water to yield the N-methylphthalimide or by dipolar cycloaddition with acetone, methyl acrylate, or acrylonitrile. Cycloadditions with the latter two dipolarophiles are both regioselective and endo-stereoselective. These processes can be triplet photosensitized by use of acetophenone. The related N-[(trimethylsilyl)methyl]-1,8-naphthalimide reacts in a similar manner upon irradiation in MeCN solutions containing the dipolarophiles methyl acrylate and acrylonitrile to produce cycloadducts which undergo spontaneous elimination of TMSOH, yielding alpha,beta-unsaturated ester or nitrile products. The ylide formed by irradiation of the (silylmethyl)phthalimide is trapped in a stereospecific (retention) manner by the dipolarophiles trans-hex-4-en-3-one, dimethyl maleate, and dimethyl fumarate. The effect of aryl ring substitution on the regiochemical course of the photoinduced C to O silyl migration process was probed by use of the 4-methoxy- and 4-carbomethoxyl-N-(silylmethyl)phthalimides. Irradiation of the former substance in an MeCN solution containing acrylonitrile gives rise to a single adduct whose structure suggests that silyl migration to oxygen of the carbonyl meta to the OMe substituent is highly favored. In contrast, the 4-carbomethoxyphthalimide is converted under these conditions to a mixture of regioisomeric adducts. Thus, silyl migration in the excited state of this substance is nonselective. In accord with hints found in earlier observations made by Kanaoka (Chem. Pharm. Bull. 1982, 30, 1263), N-phthalimide derivatives of the alpha-amino acids glycine, alanine, and phenylalanine undergo similar ylide forming photoreactions upon irradiation in MeCN solutions. The azomethine ylides produced by photodecarboxylation of these substances are efficiently trapped by dipolarophiles, and the overall photoreactions starting with the alanine and phenylalanine derivatives are highly stereoselective. Finally, the N-phthalimide derivative of 2-amino-1-phenylethanol also is transformed to a related ylide upon irradiation in MeCN. The nature, regiochemical and stereochemical course, and mechanistic interpretation of these new azomethine ylide forming photoreactions are discussed in this publication.
• Directive Effects of Substituents on the Electron Transfer Photoreduction of N-Methylphthalimide by 2,3-Dimethyl-2-butene
  作者：Paul H. Mazzocchi、Frederich Khachik

  DOI：10.1016/s0040-4039(00)81795-5

  日期：1983.1