bis(4,5,6,7-tetrahydro-2H-isoindolyl)methane | 165247-13-2

• 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: bis(4,5,6,7-tetrahydro-2H-isoindolyl)methane
• 英文别名: 1-(4,5,6,7-tetrahydro-2H-isoindol-1-ylmethyl)-4,5,6,7-tetrahydro-2H-isoindole
• CAS: 165247-13-2
• 化学式: C₁₇H₂₂N₂
• 分子量: 254.375
• InChiKey: SQNMXBZETVSPAE-UHFFFAOYSA-N

物化性质

• 沸点：
  460.2±40.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  bis(4,5,6,7-tetrahydro-2H-isoindolyl)methane 在 四苯基环戊二烯酮 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  一类中介二苯基取代四苯并卟吩衍生物及其在医药与材料领域的应用

  摘要：

  本发明涉及一类新型中介二苯基取代四苯并卟吩衍生物，其特征是具有下述结构（I）：#imgabs0#本发明涉及光敏药物与光动力疗法领域，尤其是一类新的中介二苯基取代四苯并卟吩衍生物（化合物I），研究表明：经改造后的新化合物中介二苯基取代四苯并卟吩衍生物均对人食管癌细胞均有光动力抑制作用；与上市药物相比，新化合物结构单一且稳定、制备工艺较为简便，在400‑750 nm之间有显著多波长吸收，可用于不同体积或不同深度的肿瘤的治疗，从而实现治疗的个性化与精准化。因此，新研制的化合物具有发展为肿瘤、视网膜黄斑变性、光化性角化病、鲜红斑痣、尖锐湿疣等疾病的光动力药物前景。

  公开号：

  CN117384174A
• 作为产物：
  描述：

  bis(3-ethoxycarbonyl-4,5,6,7-tetrahydro-2H-isoindolyl)methane 在 乙二醇 、 potassium hydroxide 作用下， 反应 0.5h， 生成 bis(4,5,6,7-tetrahydro-2H-isoindolyl)methane
  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

文献信息

• 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.
• 10.1016/j.bioorg.2024.107710
  作者：Mi, Le、Yan, Yi-Jia、Li, Man-Yi、Xu, Tao、Namulinda, Tabbisa、Meerovich, Gennady A.、Reshetov, Igor V.、Kogan, Evgeniy A.、Atassi, Yomen、Chen, Zhi-Long

  DOI：10.1016/j.bioorg.2024.107710

  日期：——
• Retooling Manganese(III) Porphyrin-Based Peroxynitrite Decomposition Catalysts for Selectivity and Oral Activity: A Potential New Strategy for Treating Chronic Pain
  作者：Smita Rausaria、Mahsa M. E. Ghaffari、Andrew Kamadulski、Kenny Rodgers、Leesa Bryant、Zhoumou Chen、Tim Doyle、Michael J. Shaw、Daniela Salvemini、William L. Neumann

  DOI：10.1021/jm201233r

  日期：2011.12.22

  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.