Synthesis of Chiral Macrocyclic or Linear Pyridine Carboxamides from Pyridine-2,6-dicarbonyl Dichloride as Antimicrobial Agents

doi:10.3390/molecules15096588

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Molecules 2010, 15(9), 6588-6597; doi:10.3390/molecules15096588

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Synthesis of Chiral Macrocyclic or Linear Pyridine Carboxamides from Pyridine-2,6-dicarbonyl Dichloride as Antimicrobial Agents

Rashad A. Al-Salahi, Mohamed A Al-Omar and Abd El-Galil E Amr*

Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia

* Author to whom correspondence should be addressed.

Received: 26 August 2010; in revised form: 6 September 2010 / Accepted: 7 September 2010 / Published: 20 September 2010

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Abstract: A series of chiral linear and macrocyclic bridged pyridines has been prepared starting from pyridine-2,6-dicarbonyl dichloride (2). The coupling of 1 with D-alanyl methyl ester gave 2,6-bis-D-alanyl pyridine methyl ester (3). Hydrazinolysis of 3 with hydrazine hydrate afforded bis-hydrazide 4. The latter was reacted with thiophene-2-carbaldehyde, phthalic anhydride or cyclohexanone to afford bis-carboxamide pyridine derivatives 5-7, respectively. Compound 4 was coupled with p-methoxy- or p-nitroaceto-phenone to yield compounds 8 and 9. In addition, 4 was reacted with 1,2,4,5-benzenetetra-carboxylic acid dianhydride or 1,4,5,8-naphthalenetetracarboxylic acid dianhydride to afford the macrocyclic octacarboxaamide pyridines 10 and 11. The detailed synthesis, spectroscopic data and antimicrobial screening for the synthesized compounds are reported.

Keywords: synthesis; chiral macrocyclic; pyridine-2,6-dicarbonyl dichloride; antimicrobial activity

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MDPI and ACS Style

Al-Salahi, R.A.; Al-Omar, M.A.; Amr, A.-G.E. Synthesis of Chiral Macrocyclic or Linear Pyridine Carboxamides from Pyridine-2,6-dicarbonyl Dichloride as Antimicrobial Agents. Molecules 2010, 15, 6588-6597.

AMA Style

Al-Salahi RA, Al-Omar MA, Amr A-GE. Synthesis of Chiral Macrocyclic or Linear Pyridine Carboxamides from Pyridine-2,6-dicarbonyl Dichloride as Antimicrobial Agents. Molecules. 2010; 15(9):6588-6597.

Chicago/Turabian Style

Al-Salahi, Rashad A.; Al-Omar, Mohamed A.; Amr, Abd El-Galil E. 2010. "Synthesis of Chiral Macrocyclic or Linear Pyridine Carboxamides from Pyridine-2,6-dicarbonyl Dichloride as Antimicrobial Agents." Molecules 15, no. 9: 6588-6597.

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