双(2-N-吡咯基苯基)二硫化物 | 43153-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 双(2-N-吡咯基苯基)二硫化物
• 英文名称: bis(2-N-pyrrolylphenyl) disulfide
• 英文别名: bis(2-pyrrolophenyl)disulfide；1,1'-(2,2'-disulfanediyl-diphenyl)-bis-pyrrole；Bis-(2-N-pyrrolyl-phenyl)-disulfid；1-[2-[(2-Pyrrol-1-ylphenyl)disulfanyl]phenyl]pyrrole
• CAS: 43153-75-9
• 化学式: C₂₀H₁₆N₂S₂
• 分子量: 348.492
• InChiKey: SHQHEWOIPIAKJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  双(2-N-吡咯基苯基)二硫化物 在 sodium hydroxide 、 sodium tetrahydroborate 、 五氯化磷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 78.0h， 生成 6-(p-chlorophenyl)pyrrolo<2,1-d><1,5>benzothiazepin-7(6H)-one
  参考文献：
  名称：

  A Comparative Molecular Field Analysis Model for 6-Arylpyrrolo[2,1-d][1,5]benzothiazepines Binding Selectively to the Mitochondrial Benzodiazepine Receptor

  摘要：

  A series of 42 6-arylpyrrolo[2,1-d][1,5]benzothiazepines which we have recently described as selective ligands of the mitochondrial benzodiazepine receptor (MBR) (Fiorini I.; et al. J. Med. Chem. 1994, 37, 1427-1438), have been investigated using the comparative molecular field analysis (CoMFA) approach. The resulting 3D-QSAR model rationalizes the steric and electronic factors which modulate affinity to the MBR with a cross-validation standard error of 0.648 pIC(50) unit. A set of seven novel pyrrolobenzothiazepine congeners has successively been synthesized and tested. The CoMFA model forecasts the binding affinity values of these new compounds with a prediction standard error of 0.536.

  DOI：

  10.1021/jm00050a007
• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 双(2-氨基苯基)二硫 在 溶剂黄146 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 以86 %的产率得到双(2-N-吡咯基苯基)二硫化物
  参考文献：
  名称：

  Four-Component Ring-Opening Reaction of Pyrroles via C–N Bond Cleavage under Multiple Functions of Elemental Sulfur

  摘要：

  DOI：

  10.1021/acs.orglett.3c00945

文献信息

• Novel Ligands Specific for Mitochondrial Benzodiazepine Receptors: 6-arylpyrrolo[2,1-d][1,5]benzothiazepine Derivatives. Synthesis, Structure-Activity Relationships, and Molecular Modeling Studies
  作者：Isabella Fiorini、Vito Nacci、Silvia Maria Ciani、Antonio Garofalo、Giuseppe Campiani、Luisa Savini、Ettore Novellino、Gianni Greco、Paola Bernasconi、Tiziana Mennini

  DOI：10.1021/jm00036a007

  日期：1994.5

  important structural features improving affinity. Therefore, 7-[(dimethylcarbamoyl)oxy]- and 7-acetoxy-4-chloro-6-phenylpyrrolo[2,1-d][1,5]benzothiazepine (43 and 57) were synthesized. With 7-[(dimethylcarbamoyl)oxy]-6-(p-methoxyphenyl)pyrrolo[2,1- d][1,5]benzothiazepine (65), these were the most promising compounds with IC50s of respectively 9, 8, and 9 nM, under conditions where PK 11195 had an IC50

  已鉴定出一类新的对MBR受体具有特异性的配体：6-芳基吡咯并[2,1-d] [1,5]苯并硫氮杂derivatives衍生物。大多数新合成的酯37-64以及一些中间酮对[3H] PK 11195的结合抑制表现出微摩尔或纳摩尔的亲和力。一项对42种化合物的SAR研究和分子建模方法得出了初步的结构选择性特征：6,7-双键，7位的氨基甲酰氧基，alcanoyloxy和甲磺酰氧基侧链以及4位的预期氯取代位置似乎是提高亲和力的最重要的结构特征。因此，合成了7-[（（二甲基氨基甲酰基）氧基]-和7-乙酰氧基-4-氯-6-苯基吡咯并[2，1-d] [1，5]苯并硫氮杂（（43和57）。与7-[（二甲基氨基甲酰基）氧基] -6-（对甲氧基苯基）吡咯并[2,1- d] [1,5]苯并噻氮平（65），
• Non-Nucleoside Inhibitors of Human Adenosine Kinase: Synthesis, Molecular Modeling, and Biological Studies
  作者：Stefania Butini、Sandra Gemma、Margherita Brindisi、Giuseppe Borrelli、Andrea Lossani、Anna Maria Ponte、Andrea Torti、Giovanni Maga、Luciana Marinelli、Valeria La Pietra、Isabella Fiorini、Stefania Lamponi、Giuseppe Campiani、Daniela M. Zisterer、Seema-Maria Nathwani、Stefania Sartini、Concettina La Motta、Federico Da Settimo、Ettore Novellino、Federico Focher

  DOI：10.1021/jm101438u

  日期：2011.3.10

  Adenosine kinase (AK) catalyzes the phosphorylation of adenosine (Ado) to AMP by means of a kinetic mechanism in which the two substrates Ado and ATP bind the enzyme in a binary and/or ternary complex, with distinct protein conformations. Most of the described inhibitors have Ado-like structural motifs and are nonselective; and some of them (e.g., the tubercidine-like ligands) are characterized by a toxic profile. We have cloned and expressed human AK (hAK) and searched for novel non-substrate-like inhibitors. Our efforts to widen the structural diversity of AK inhibitors led to the identification of novel non-nucleoside, noncompetitive allosteric modulators characterized by a unique molecular scaffold. Among the pyrrolobenzoxa(thia)zepinones (4a-qq) developed, 4a was identified as a non-nucleoside prototype hAK. inhibitor. 4a has proapoptotic efficacy, slight inhibition of short-term RNA synthesis, and cytostatic activity on tumor cell lines while showing low cytotoxicity and no significant adverse effects on short-term DNA synthesis in cells.
• Bates, Dallas K.; Winters, R. Thomas; Burnell, A. Sell, Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 695 - 699
  作者：Bates, Dallas K.、Winters, R. Thomas、Burnell, A. Sell

  DOI：——

  日期：——
• A Comparative Molecular Field Analysis Model for 6-Arylpyrrolo[2,1-d][1,5]benzothiazepines Binding Selectively to the Mitochondrial Benzodiazepine Receptor
  作者：Giovanni Greco、Ettore Novellino、Isabella Fiorini、Vito Nacci、Giuseppe Campiani、Silvia M. Ciani、Antonio Garofalo、Paola Bernasconi、Tiziana Mennini

  DOI：10.1021/jm00050a007

  日期：1994.11

  A series of 42 6-arylpyrrolo[2,1-d][1,5]benzothiazepines which we have recently described as selective ligands of the mitochondrial benzodiazepine receptor (MBR) (Fiorini I.; et al. J. Med. Chem. 1994, 37, 1427-1438), have been investigated using the comparative molecular field analysis (CoMFA) approach. The resulting 3D-QSAR model rationalizes the steric and electronic factors which modulate affinity to the MBR with a cross-validation standard error of 0.648 pIC(50) unit. A set of seven novel pyrrolobenzothiazepine congeners has successively been synthesized and tested. The CoMFA model forecasts the binding affinity values of these new compounds with a prediction standard error of 0.536.
• Four-Component Ring-Opening Reaction of Pyrroles via C–N Bond Cleavage under Multiple Functions of Elemental Sulfur
  作者：Zongkang Wang、Ye Wang、Yang Yuan、Yingge Gu、Yilin Zhu、Lijie Liu、Ziyi Zhuang、Lingkai Kong、Yanzhong Li

  DOI：10.1021/acs.orglett.3c00945

  日期：2023.5.5