Literature DB >> 19679380

Design and one-pot synthesis of alpha-aminophosphonates and bis(alpha-aminophosphonates) by iron(III) chloride and cytotoxic activity.

Zahra Rezaei1, Habib Firouzabadi, Nasser Iranpoor, Abbas Ghaderi, Mohammad Reza Jafari, Abbas Ali Jafari, Hamid Reza Zare.   

Abstract

In this study, we used a solution of FeCl(3) in THF to facilitate the Mannich-type reaction of aldehyde, amine and phosphite compounds to form corresponding alpha-aminophosphonates in a one-pot, three-component reaction. Selected alpha-aminophosphonates were entered into a biological assay test and were studied by docking methods, using Autodock 3.0. The results showed that the reactions were carried out mildly and eco-friendly to form alpha-aminophosphonates in high yields. Some were found to have cytotoxic activity on the cell lines RAJI, JURKAT and MCF-7. An indole derived bis(alpha-aminophosphonates) showed maximum cytotoxic effect comparable to doxorubicin. Although the FDE (Final Docking Energy) for the most cytotoxic compound was of the most negative value, there is no correlation between FDE and cytotoxicity.

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Year:  2009        PMID: 19679380     DOI: 10.1016/j.ejmech.2009.07.009

Source DB:  PubMed          Journal:  Eur J Med Chem        ISSN: 0223-5234            Impact factor:   6.514


  11 in total

Review 1.  Mannich bases in medicinal chemistry and drug design.

Authors:  Gheorghe Roman
Journal:  Eur J Med Chem       Date:  2014-10-30       Impact factor: 6.514

2.  Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates.

Authors:  Zahra Rezaei; Soghra Khabnadideh; Kamiar Zomorodian; Keyvan Pakshir; Setareh Nadali; Nadia Mohtashami; Ehsan Faghih Mirzaei
Journal:  Int J Med Chem       Date:  2011-09-26

3.  A highly efficient bismuth salts-catalyzed route for the synthesis of α-aminophosphonates.

Authors:  Antara Banik; Sahil Batta; Debasish Bandyopadhyay; Bimal K Banik
Journal:  Molecules       Date:  2010-11-12       Impact factor: 4.411

4.  New 2-Oxoindolin Phosphonates as Novel Agents to Treat Cancer: A Green Synthesis and Molecular Modeling.

Authors:  Shailee V Tiwari; Nawaz S Sharif; Rekha I Gajare; Julio A Seijas Vazquez; Jaiprakash N Sangshetti; Manoj D Damale; Anna Pratima G Nikalje
Journal:  Molecules       Date:  2018-08-08       Impact factor: 4.411

5.  Cobalt Catalyzed C-P Bond Formation by Cross-Coupling of Boronic Acids with P(O)H Compounds in Presence of Zinc.

Authors:  Ian Hicks; Jonathan McTague; Tatiana Hapatsha; Rania Teriak; Parminder Kaur
Journal:  Molecules       Date:  2020-01-10       Impact factor: 4.411

6.  Green Synthesis, Antioxidant, and Plant Growth Regulatory Activities of Novel α-Furfuryl-2-alkylaminophosphonates.

Authors:  Maheshwara Reddy Nadiveedhi; Poojith Nuthalapati; Mohan Gundluru; Mohan Reddy Yanamula; Saritha Venkatareddy Kallimakula; Visweswara Rao Pasupuleti; Vijaya Kumar Reddy Avula; Swetha Vallela; Grigory Vasilievich Zyryanov; Satheesh Krishna Balam; Suresh Reddy Cirandur
Journal:  ACS Omega       Date:  2021-01-21

7.  Synthesis, structural studies and biological properties of some phosphono-perfluorophenylalanine derivatives formed by SNAr reactions.

Authors:  Joanna Kwiczak-Yiğitbaşı; Jean-Luc Pirat; David Virieux; Jean-Noël Volle; Agnieszka Janiak; Marcin Hoffmann; Jakub Mrzygłód; Dariusz Wawrzyniak; Jan Barciszewski; Donata Pluskota-Karwatka
Journal:  RSC Adv       Date:  2019-08-05       Impact factor: 4.036

8.  One-pot synthesis of α-aminophosphonates by yttrium-catalyzed Birum-Oleksyszyn reaction.

Authors:  Davide Ceradini; Kirill Shubin
Journal:  RSC Adv       Date:  2021-12-08       Impact factor: 4.036

9.  Discovery of ( ±)-3-(1H-pyrazol-1-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazine derivatives with promising in vitro anticoronavirus and antitumoral activity.

Authors:  Parameshwara Chary Jilloju; Leentje Persoons; Sathish Kumar Kurapati; Dominique Schols; Steven De Jonghe; Dirk Daelemans; Rajeswar Rao Vedula
Journal:  Mol Divers       Date:  2021-06-24       Impact factor: 2.943

10.  Synthesis and Biological Evaluation of Novel Indole-Derived Thioureas.

Authors:  Giuseppina Sanna; Silvia Madeddu; Gabriele Giliberti; Sandra Piras; Marta Struga; Małgorzata Wrzosek; Grażyna Kubiak-Tomaszewska; Anna E Koziol; Oleksandra Savchenko; Tadeusz Lis; Joanna Stefanska; Piotr Tomaszewski; Michał Skrzycki; Daniel Szulczyk
Journal:  Molecules       Date:  2018-10-07       Impact factor: 4.411

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