bis(3-ethoxycarbonyl-4,5,6,7-tetrahydro-2H-isoindolyl)methane | 1029092-38-3

• 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: bis(3-ethoxycarbonyl-4,5,6,7-tetrahydro-2H-isoindolyl)methane
• 英文别名: bis(3-carbethoxy-4,5,6,7-tetrahydro-2H-isoindolyl)methane；diethyl 3,3'-methylenebis(4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate)；ethyl 3-[(3-ethoxycarbonyl-4,5,6,7-tetrahydro-2H-isoindol-1-yl)methyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate
• CAS: 1029092-38-3
• 化学式: C₂₃H₃₀N₂O₄
• 分子量: 398.502
• InChiKey: YKABSNPCVQYIGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(3-ethoxycarbonyl-4,5,6,7-tetrahydro-2H-isoindolyl)methane 在 乙二醇 、 三氟乙酸 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 生成 5,15-diphenyltetracyclohexenoporphyrin
  参考文献：
  名称：

  Retooling Manganese(III) Porphyrin-Based Peroxynitrite Decomposition Catalysts for Selectivity and Oral Activity: A Potential New Strategy for Treating Chronic Pain

  摘要：

  Redox-active metalloporphyrins represent the most well-characterized class of catalysts capable of attenuating oxidative stress in vivo through the direct interception and decomposition of superoxide and peroxynitrite. While many interesting pharmacological probes have emerged from these studies, few catalysts have been developed with pharmaceutical properties in mind. Herein, we describe our efforts to identify new Mn(III) porphyrin systems with enhanced membrane solubilizing properties. To this end, seven new Mn(III)-tetracyclohexenylporphyin (TCHP) analogues, 7, 10, 12, 15, and 16a-c, have been prepared in which the beta-fused cyclohexenyl rings provide a means to shield the charged metal center from the membrane during passive transport. Compounds 7, 15, and 16a-c have been shown to be orally active and potent analgesics in a model of carrageenan-induced thermal hyperalgesia. In addition, oral administration of compound 7 (10 100 mg/kg, n = 5) has been shown to dose dependently reverse mechano-allodynia in the CCI model of chronic neuropathic pain.

  DOI：

  10.1021/jm201233r
• 作为产物：
  描述：

  [(2-Iodocyclohexyl)sulfonyl]benzene 在 aluminum oxide 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 bis(3-ethoxycarbonyl-4,5,6,7-tetrahydro-2H-isoindolyl)methane
  参考文献：
  名称：

  Synthesis and evaluation of 5,15-diaryltetrabenzoporphyrins as photosensitizers for photo-diagnosis and photodynamic activity of tumors

  摘要：

  DOI：

  10.1016/j.bioorg.2024.107710

文献信息

• Synthesis, Computational Modeling, and Properties of Benzo-Appended BODIPYs
  作者：Timsy Uppal、Xiaoke Hu、Frank R. Fronczek、Stephanie Maschek、Petia Bobadova-Parvanova、M. Graça H. Vicente

  DOI：10.1002/chem.201103002

  日期：2012.3.26

  and dibenzo‐appended BODIPY dyes were synthesized from a common tetrahydroisoindole precursor following two different synthetic routes. Route A involved the assembly of the BODIPY core prior to aromatization, while in Route B the aromatization step was performed first. In general, Route A gave higher yields of the target dibenzo‐BODIPYs, due to the ease of aromatization of the BODIPYs compared with

  遵循两种不同的合成路线，从一种常见的四氢异吲哚前体合成了一系列新型的官能化的单和二苯并苯并并附上的BODIPY染料。路线A涉及在芳构化之前组装BODIPY核芯，而在路线B中，首先进行芳构化步骤。通常，由于BODIPYs的芳构化要比相应的二吡咯烷酮容易，路线A给出了较高的目标二苯并-BODIPYs产量，这可能是由于它们在氧化条件下具有更高的稳定性（2,3-dichloro-5,6 -二氰基-1,4-苯醌在回流的甲苯中）。但是，由于带有介孔C 6 F 5基团的高度缺电子的BODIPY 3 c的缓慢氧化，因此二苯并-BODIPY 4 c仅通过路线B从二吡咯甲烷中获得了35％的总量。在6-31G（d，p）水平上进行的计算计算与实验结果相符，显示出两种路线中所有反应中间体的相似相对能量。另外，BODIPY 3 c具有最高的分子静电势（MEPN），证实了其高电子缺乏性和随之而来的抗氧化性。对八个BOD
• Synthesis of 5,15-Diaryltetrabenzoporphyrins
  作者：Mikhail A. Filatov、Artem Y. Lebedev、Sergei A. Vinogradov、Andrei V. Cheprakov

  DOI：10.1021/jo800509k

  日期：2008.6.1

  A general method of synthesis of 5,15-diaryltetrabenzoporphyrins (Ar(2)TBPs) has been developed, based on 2 + 2 condensation of dipyrromethanes followed by oxidative aromatization. Two pathways to Ar(2)TBPs were investigated: the tetrahydroisoindole pathway and the dihydroisoindole pathway. In the tetrahydroisoindole pathway, precursor 5,15-diaryltetracyclohexenoporphyrins (5,15-Ar(2)TCHPs) were assembled from cyclohexeno-fused meso-unsubstituted dipyrromethanes and aromatic aldehydes or, alternatively, by way of the classical MacDonald synthesis. In the first case, scrambling was observed. Aromatization by tetracyclone was more effective than aromatization by DDQ but failed in the cases of porphyrins with electron-withdrawing substituents in the meso-aryl rings. The dihydroisoindole pathway was found to be much superior to the tetrahydroisoindole pathway, and it was developed into a general preparative method, consisting of (1) the synthesis of 4,7-dihydroisoindole and its transformation into meso-unsubstituted dipyrromethanes, (2) the synthesis of 5,15-diaryloctahydrotetrabenzoporphyrins (5,15-Ar(2)OHTBPs), and (3) their subsequent aromatization by DDQ. Ar2TBP free bases exhibit optical absorption spectra similar to those of meso-unsubstituted tetrabenzoporphyrins and fluoresce with high quantum yields. Pd complex of Ph2TBP was found to be highly phosphorescent at room temperature.
• METHOD FOR TREATING CHRONIC PAIN
  申请人：Salvemini Daniela

  公开号：US20120135973A1

  公开（公告）日：2012-05-31

  The present invention provides analgesic compounds comprising at least one modified metalloporphyrin compound. Also provided are methods of treating pain by orally administering an analgesic compounds comprising at least one modified metalloporphyrin compound.
• [EN] METHOD FOR TREATING CHRONIC PAIN<br/>[FR] PROCÉDÉ DE TRAITEMENT DE LA DOULEUR CHRONIQUE
  申请人：SOUTHERN ILLINOIS UNIVERSITY EDWARDSVILLE

  公开号：WO2012033916A1

  公开（公告）日：2012-03-15

  Analgesic compounds comprise at least one modified metalloporphyrin compound. Methods of treating pain by orally administering an analgesic compounds comprise at least one modified metalloporphyrin compound. Orally available peroxynitrite decomposition catalyst (PNDC) compounds are provided that are based on novel modified porphyrin structures. The modifications to the porphyrin structures render the compounds orally available and capable of crossing the blood-brain barrier (BBB), while retaining high PNDC efficacy. Examples of orally available PNDC compounds, methods of producing the PNDC compounds, and methods of using the PNDC compounds to treat chronic pain associated with neuropathic, inflammatory, or other disorders.