Next Article in Journal
A Comprehensive Review on the Phytochemical Constituents and Pharmacological Activities of Pogostemon cablin Benth.: An Aromatic Medicinal Plant of Industrial Importance
Previous Article in Journal
Isoindolinones as Michael Donors under Phase Transfer Catalysis: Enantioselective Synthesis of Phthalimidines Containing a Tetrasubstituted Carbon Stereocenter
Article Menu

Export Article

Open AccessArticle
Molecules 2015, 20(5), 8499-8520; doi:10.3390/molecules20058499

Microwave-Assisted Synthesis of Novel Pyrazolo[3,4-g][1,8]naphthyridin-5-amine with Potential Antifungal and Antitumor Activity

1
Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, A.A. 25360 Cali, Colombia
2
Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, CP 2000 Rosario, Argentina
*
Author to whom correspondence should be addressed.
Academic Editor: Maria Emília Sousa
Received: 17 April 2015 / Revised: 5 May 2015 / Accepted: 6 May 2015 / Published: 12 May 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [822 KB, uploaded 12 May 2015]   |  

Abstract

The microwave assisted reaction between heterocyclic o-aminonitriles 1 and cyclic ketones 2 catalyzed by zinc chloride led to new series of pyrazolo[3,4-b] [1,8]naphthyridin-5-amines 3 in good yields. This procedure provides several advantages such as being environmentally friendly, high yields, simple work-up procedure, broad scope of applicability and the protocol provides an alternative for the synthesis of pyrazolonaphthyridines. The whole series showed antifungal activities against Candida albicans and Cryptococcus neoformans standardized strains, being compounds with a 4-p-tolyl substituent of the naphthyridin scheleton (3a, 3d and 3g), the most active ones mainly against C. albicans, which appear to be related to their comparative hydrophobicity. Among them, 3d, containing a cyclohexyl fused ring, showed the best activity. The anti-Candida activity was corroborated by testing the three most active compounds against clinical isolates of albicans and non-albicans Candida strains. These compounds were also screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Compounds 3a and 3e showed remarkable antitumor activity against cancer cell lines, with the most important GI50 values ranging from 0.62 to 2.18 μM View Full-Text
Keywords: antifungal activity; antitumoral activity; pyrazolonaphthyridines; microwave irradiation; Candida albicans; Cryptococcus neoformans antifungal activity; antitumoral activity; pyrazolonaphthyridines; microwave irradiation; Candida albicans; Cryptococcus neoformans
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Acosta, P.; Butassi, E.; Insuasty, B.; Ortiz, A.; Abonia, R.; Zacchino, S.A.; Quiroga, J. Microwave-Assisted Synthesis of Novel Pyrazolo[3,4-g][1,8]naphthyridin-5-amine with Potential Antifungal and Antitumor Activity. Molecules 2015, 20, 8499-8520.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top