4-(5,10,10,15,15,20,20-Heptamethyl-21,22,23,24-tetrahydroporphyrin-5-yl)aniline | 1422191-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 4-(5,10,10,15,15,20,20-Heptamethyl-21,22,23,24-tetrahydroporphyrin-5-yl)aniline
• 英文别名: 4-(5,10,10,15,15,20,20-heptamethyl-21,22,23,24-tetrahydroporphyrin-5-yl)aniline
• CAS: 1422191-90-9
• 化学式: C₃₃H₃₉N₅
• 分子量: 505.706
• InChiKey: ZFXGDGRWBYXCDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  38
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.2
• 氢给体数：
  5
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-dichlorobis(dimethylsulfoxide)platinum(II) 、 4-(5,10,10,15,15,20,20-Heptamethyl-21,22,23,24-tetrahydroporphyrin-5-yl)aniline 以 二氯甲烷-D2 为溶剂， 生成 4-(5,10,10,15,15,20,20-Heptamethyl-21,22,23,24-tetrahydroporphyrin-5-yl)aniline;methylsulfinylmethane;platinum(2+);dichloride
  参考文献：
  名称：

  Drug Delivery with a Calixpyrrole–trans-Pt(II) Complex

  摘要：

  A meso-p-nitroaniline-calix[4]pyrrole derivative trans-coordinated to a Pt(II) center was synthesized and its structure solved by X-ray analysis. Adenosine monophosphate (AMP) was used as a model compound to evaluate the potential for the assisted delivery of the metal to the DNA nucleobases via the phosphate anion-binding properties of the calix[4]pyrrole unit. An NMR investigation of the kinetics of AMP complexation in the absence of an H-bonding competing solvent (dry CD3CN) was consistent with this hypothesis, but we could not detect the interaction of the calix[4]pyrrole with phosphate in the presence of water. However, in vitro tests of the new trans-calixpyrrole- Pt(II) complex on different cancer cell lines indicate a cytotoxic activity that is unquestionably derived from the coexistence of both the trans-Pt(II) fragment and the calix[4]pyrrole unit.

  DOI：

  10.1021/ja307791j
• 作为产物：
  描述：

  5,5,10,10,15,15,20-heptamethyl-20-(4-nitrophenyl)-5H,10H,15H,20H,22H,24H-porphyrin 在 palladium 10% on activated carbon 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以74%的产率得到4-(5,10,10,15,15,20,20-Heptamethyl-21,22,23,24-tetrahydroporphyrin-5-yl)aniline
  参考文献：
  名称：

  Drug Delivery with a Calixpyrrole–trans-Pt(II) Complex

  摘要：

  A meso-p-nitroaniline-calix[4]pyrrole derivative trans-coordinated to a Pt(II) center was synthesized and its structure solved by X-ray analysis. Adenosine monophosphate (AMP) was used as a model compound to evaluate the potential for the assisted delivery of the metal to the DNA nucleobases via the phosphate anion-binding properties of the calix[4]pyrrole unit. An NMR investigation of the kinetics of AMP complexation in the absence of an H-bonding competing solvent (dry CD3CN) was consistent with this hypothesis, but we could not detect the interaction of the calix[4]pyrrole with phosphate in the presence of water. However, in vitro tests of the new trans-calixpyrrole- Pt(II) complex on different cancer cell lines indicate a cytotoxic activity that is unquestionably derived from the coexistence of both the trans-Pt(II) fragment and the calix[4]pyrrole unit.

  DOI：

  10.1021/ja307791j

文献信息

• Host-Guest Chemistry of Aromatic-Amide-Linked Bis- and Tris-Calix[4]pyrroles with Bis-Carboxylates and Citrate Anion
  作者：Grazia Cafeo、Giuseppe Gattuso、Franz H. Kohnke、Georgia Papanikolaou、Aldo Profumo、Camillo Rosano

  DOI：10.1002/chem.201303265

  日期：2014.2.3

  A small library of polytopic receptors has been synthesized from meso‐p‐ and meso‐m‐aminophenylcalix[4]pyrroles and p‐ or m‐phthaloyl or trimesic chloride. Selected bis‐carboxylates and the citrate anion, which either exhibit altered distribution profiles in cancerous tissues in comparison with healthy tissues or are metabolites of carcinogenic substances (for example, trans,trans‐muconic acid from

  多面体受体的小文库已从合成内消旋- p -和内消旋-米-aminophenylcalix [4]吡咯和p -或米-phthaloyl或苯均三酰氯。选定的双羧酸根和柠檬酸根阴离子，与健康组织相比，其在癌组织中的分布特征发生了变化，或者是致癌物质的代谢产物（例如，反式，反式测试了人体苯接触产生的粘康酸作为配体。观察到各种亲和力和结合模式是杯[4]吡咯的数目和每个多位受体中酰胺单元拓扑结构的函数。通过分子建模得到的1：1配合物的结构与1 H NMR络合研究的结果非常吻合。
• Drug Delivery with a Calixpyrrole–<i>trans</i>-Pt(II) Complex
  作者：Grazia Cafeo、Grazia Carbotti、Angela Cuzzola、Marina Fabbi、Silvano Ferrini、Franz H. Kohnke、Georgia Papanikolaou、Maria Rosaria Plutino、Camillo Rosano、Andrew J. P. White

  DOI：10.1021/ja307791j

  日期：2013.2.20

  A meso-p-nitroaniline-calix[4]pyrrole derivative trans-coordinated to a Pt(II) center was synthesized and its structure solved by X-ray analysis. Adenosine monophosphate (AMP) was used as a model compound to evaluate the potential for the assisted delivery of the metal to the DNA nucleobases via the phosphate anion-binding properties of the calix[4]pyrrole unit. An NMR investigation of the kinetics of AMP complexation in the absence of an H-bonding competing solvent (dry CD3CN) was consistent with this hypothesis, but we could not detect the interaction of the calix[4]pyrrole with phosphate in the presence of water. However, in vitro tests of the new trans-calixpyrrole- Pt(II) complex on different cancer cell lines indicate a cytotoxic activity that is unquestionably derived from the coexistence of both the trans-Pt(II) fragment and the calix[4]pyrrole unit.