Tinto, Francesco (2017) Design and chemical synthesis of heterocyclic alkaloid compounds isolated from marine organisms. [Tesi di dottorato]

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Item Type: Tesi di dottorato
Lingua: English
Title: Design and chemical synthesis of heterocyclic alkaloid compounds isolated from marine organisms
Creators:
CreatorsEmail
Tinto, Francescofrancescotinto88@gmail.com
Date: 9 April 2017
Number of Pages: 134
Institution: Università degli Studi di Napoli Federico II
Department: Scienze Chimiche
Dottorato: Scienze chimiche
Ciclo di dottorato: 29
Coordinatore del Corso di dottorato:
nomeemail
Paduano, Luigilpaduano@unina.it
Tutor:
nomeemail
De Castro, CristinaUNSPECIFIED
Manzo, EmilianoUNSPECIFIED
Date: 9 April 2017
Number of Pages: 134
Uncontrolled Keywords: Alkaloids; parazoanthines; synthesis; heterocyclic; receptor; hydantoin; guanidine; CXCR4; cancer; HIV-1; pharmacology; chemistry; marine organisms; chemical synthesis; CXCL12; heterocyclic alkaloid; molecular docking; antagonist; CXCR4 antagonist
Settori scientifico-disciplinari del MIUR: Area 03 - Scienze chimiche > CHIM/06 - Chimica organica
Date Deposited: 03 May 2017 17:21
Last Modified: 14 Mar 2018 10:07
URI: http://www.fedoa.unina.it/id/eprint/11673
DOI: 10.6093/UNINA/FEDOA/11673

Abstract

Alkaloids are naturally occurring nitrogen containing biologically active heterocyclic compounds. Over the last years, a large number of biologically alkaloids with antiviral, antibacterial, anti-inflammatory, antimalarial, antioxidant and anticancer activities have been isolated from marine source. In this frame parazoanthines are a group of unique naturally-occurring marine alkaloids reported to date only from the Mediterranean sea anemone Parazoanthus axinellae. The chemical framework characteristic of these molecules is a 3,5-alkyl disubstituted hydantoin core bearing a terminal guanidine and an aromatic ring. Hydantoins and derivatives have been widely used in biomedical studies including novel therapeutic agents of interest as anti-convulsants and antimuscarinics,antiulcers and antiarrythmics, antivirals, antidiabetics, and inhibitors of antagonist of serotonin and fibrinogen receptors, inhibitors of glycine binding site of the NMDA receptor and antagonists of leukocyte cell adhesion. Due to the biological potential of this class of molecules, a synthetic strategy was planed and developed to prepare natural and not natural analogs of parazoanthines; the molecular docking tests have described a promising antagonist activity on co-chemokine receptor CXCR4, involved in many tumors (breast cancer, melanoma, leukemia multiple myeloma, small cell lung cancer (SCLC), malignant melanoma and pancreatic cancer), rheumatoid arthritis, stem cell mobilization and HIV-1. The preliminary tests in vitro have confirmed the antagonist effect of parazoanthine-A with the co-receptor CXCR4, describing a promising pharmacological action for the treatment of diseases involved by the activation of this receptor.

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