2,5-bis(4-formylphenyl)furan | 214216-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 2,5-bis(4-formylphenyl)furan
• 英文别名: 4-[5-(4-Formylphenyl)furan-2-yl]benzaldehyde
• CAS: 214216-23-6
• 化学式: C₁₈H₁₂O₃
• 分子量: 276.291
• InChiKey: UKRXSSLKCJQRSI-UHFFFAOYSA-N

物化性质

• 沸点：
  460.597±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.222±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(N-isopropylamidino)-1,2-phenylene diamine 、 2,5-bis(4-formylphenyl)furan 在 对苯醌 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 8:4,4'-bis[2-[5-(N-isopropylamidino)benzimidazoyl]]-2,5-diphenylfuran
  参考文献：
  名称：

  Extended Aromatic Furan Amidino Derivatives as Anti-Pneumocystis carinii Agents

  摘要：

  The. syntheses of nine new derivatives of 2,5-bis[4-(N-alkylamidino)phenyl]furans with extended aromatic systems are reported. The interaction of these dicationic furans with poly(dA)*poly(dT) and with the duplex oligomers d(CGCGAATTCGCG)(2) and d(GCGAATTCGC)(2) was determined by T(m) measurement, and the effectiveness of these compounds against the immunosuppressed rat model of Pneumocystis carinii was evaluated. At a screening dose of 10 mu mol/kg, 4 of the 12 amidino furans described here are more active than the parent compound 1. In general, extension of the aromatic system in the absence of a substitution of the amidino nitrogens resulted in higher affinity for DNA than the parent compound as judged by the larger Delta T(m) values and suggests enhanced van der Waals interactions in the amidino furan-DNA complex. Three of the compounds, 3, 5, and 11, yield cysts counts of less than 0.1% of control when administered at a dosage of 10 mu mol/kg. Compound 3, which does not have an extended aromatic system, is the most active derivative. Although a direct correlation between anti-P. carinii activity and DNA binding affinity was not observed, all compounds which have significant activity have large Delta T(m) values.

  DOI：

  10.1021/jm980230c
• 作为产物：
  描述：

  4,4'-(2,5-呋喃二基)二-苯甲腈 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到2,5-bis(4-formylphenyl)furan
  参考文献：
  名称：

  Structure-In Vitro Activity Relationships of Pentamidine Analogues and Dication-Substituted Bis-Benzimidazoles as New Antifungal Agents

  摘要：

  摘要：对于20种戊二胺类似物、7种戊二胺的主要代谢产物以及30种二阳离子取代的双苯并咪唑类化合物进行了筛选，评估它们对念珠菌和隐球菌的抑制和杀真菌活性。大多数化合物的MIC（80%菌株被抑制的最小抑菌浓度）与两性霉素B和氟康唑相当。与氟康唑不同，许多这些化合物表现出强效的杀真菌活性。对于念珠菌而言，最有效的化合物的MIC80为≤0.09μg/ml，对于隐球菌而言，最有效的化合物的MIC80为0.19μg/ml。选择的化合物也对曲霉、索兰镰孢霉、除念珠菌外的其他种类的念珠菌，以及氟康唑耐药菌株的活性。从这里呈现的数据清楚地表明，有必要进行进一步的研究，以确定这些化合物的结构活性关系、作用机制和毒性，以及它们在体内的疗效，以确定它们的临床潜力。

  DOI：

  10.1128/aac.42.10.2495

文献信息

• Antifungal activity of dicationic molecules
  申请人：UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1685836A2

  公开（公告）日：2006-08-02

  Methods of treating fungal infections comprise administering a therapeutically effective amount of a compound described by Formulas [(I)-(II)]. Examples of fungal infections include Candida albicans, Cryptococcus neoformans, Aspergillus fumigatus, Fusarium solani, and combinations thereof.

  治疗真菌感染的方法包括施用治疗有效量的式[(I)-(II)]所述化合物。真菌感染的例子包括白色念珠菌、新生隐球菌、烟曲霉、梭菌及其组合。
• ANTIFUNGAL ACTIVITY OF DICATIONIC MOLECULES
  申请人：UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1143959A2

  公开（公告）日：2001-10-17
• US6326395B1
  申请人：——

  公开号：US6326395B1

  公开（公告）日：2001-12-04
• [EN] ANTIFUNGAL ACTIVITY OF DICATIONIC MOLECULES<br/>[FR] ACTIVITE ANTIFONGIQUE DE MOLECULES DICATIONIQUES
  申请人：UNIV NORTH CAROLINA

  公开号：WO2000015212A2

  公开（公告）日：2000-03-23

  Methods of treating fungal infections comprise administering a therapeutically effective amount of a compound described by Formulas (I-VI). Examples of fungal infections include Candida albicans, Cryptococcus neoformans, Aspergillus fumigatus, Fusarium solani, and combinations thereof.
• Extended Aromatic Furan Amidino Derivatives as Anti-<i>Pneumocystis carinii</i> Agents
  作者：Katherine T. Hopkins、W. David Wilson、Brendan C. Bender、Donald R. McCurdy、James Edwin Hall、Richard R. Tidwell、Arvind Kumar、Miro Bajic、David W. Boykin

  DOI：10.1021/jm980230c

  日期：1998.9.1

  The. syntheses of nine new derivatives of 2,5-bis[4-(N-alkylamidino)phenyl]furans with extended aromatic systems are reported. The interaction of these dicationic furans with poly(dA)*poly(dT) and with the duplex oligomers d(CGCGAATTCGCG)(2) and d(GCGAATTCGC)(2) was determined by T(m) measurement, and the effectiveness of these compounds against the immunosuppressed rat model of Pneumocystis carinii was evaluated. At a screening dose of 10 mu mol/kg, 4 of the 12 amidino furans described here are more active than the parent compound 1. In general, extension of the aromatic system in the absence of a substitution of the amidino nitrogens resulted in higher affinity for DNA than the parent compound as judged by the larger Delta T(m) values and suggests enhanced van der Waals interactions in the amidino furan-DNA complex. Three of the compounds, 3, 5, and 11, yield cysts counts of less than 0.1% of control when administered at a dosage of 10 mu mol/kg. Compound 3, which does not have an extended aromatic system, is the most active derivative. Although a direct correlation between anti-P. carinii activity and DNA binding affinity was not observed, all compounds which have significant activity have large Delta T(m) values.