Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms

Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms Publisher Pubmed

Hakimelahi GH^{1, 2} ; Li PC¹ ; Moosavimovahedi AA³ ; Chamani J³ ; Khodarahmi GA⁴ ; Ly TW¹ ; Valiyev F¹ ; Leong MK² ; Hakimelahi S¹ ; Shia KS² ; Chao I¹

Show Affiliations

1. Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan
2. TaiGen Biotechnology, Taipei 114, 138 Shin Ming Rd., Taiwan
3. Institute of Biochemistry-Biophysics, Tehran University, Tehran, Iran
4. Department of Medicinal Chemistry, Faculty of Pharmacy, Isfahan Univ. of Medical Sciences, Isfahan, Iran

Source: Organic and Biomolecular Chemistry Published:2003

Abstract

Racemic 7-(phenylacetamido)-1-dethia-3-aza-1-carba-2-oxacephem 3 was synthesized and found to possess antibacterial activity against Staphylococcus aureus PDA 209P, Escherichia coli ATCC 39188, Pseudomonas aeruginosa 1101-75 and Klebsiella pneumoniae NCTC 418 as well as the β-lactamase producing organisms E. coli A9675 and P. aeruginosa 18S-H and the methicillin-resistant organism S. aureus 95. Formation of the carbacephem 3 originated from the Barton photochemical reaction in the conversion of 8 to 10. Intramolecular cyclization of syn-oximino β-lactam 10 afforded 7-azido-2-oxa-3-azacephem 11, which was reduced and acylated to 12. Enzymatic removal of the methyl group from 12 gave the target molecule 3.

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Ghadamali Khodarahmi (3)

Lotfollah Saghaie Dehkordi (2)

Style	Citing Format
MLA	Hakimelahi GH, et al.. "Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms." Organic and Biomolecular Chemistry, vol. 1, no. 14, 2003, pp. 2461-2467.
APA	Hakimelahi GH, Li PC, Moosavimovahedi AA, Chamani J, Khodarahmi GA, Ly TW, Valiyev F, Leong MK, Hakimelahi S, Shia KS, Chao I (2003). Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms. Organic and Biomolecular Chemistry, 1(14), 2461-2467.
Chicago	Hakimelahi GH, Li PC, Moosavimovahedi AA, Chamani J, Khodarahmi GA, Ly TW, Valiyev F, et al.. "Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms." Organic and Biomolecular Chemistry 1, no. 14 (2003): 2461-2467.
Harvard	Hakimelahi GH et al. (2003) 'Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms', Organic and Biomolecular Chemistry, 1(14), pp. 2461-2467.
Vancouver	Hakimelahi GH, Li PC, Moosavimovahedi AA, Chamani J, Khodarahmi GA, Ly TW, et al.. Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms. Organic and Biomolecular Chemistry. 2003;1(14):2461-2467.
BibTex	@article{ author = {Hakimelahi GH and Li PC and Moosavimovahedi AA and Chamani J and Khodarahmi GA and Ly TW and Valiyev F and Leong MK and Hakimelahi S and Shia KS and Chao I}, title = {Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms}, journal = {Organic and Biomolecular Chemistry}, volume = {1}, number = {14}, pages = {2461-2467}, year = {2003} }
RIS	TY - JOUR AU - Hakimelahi GH AU - Li PC AU - Moosavimovahedi AA AU - Chamani J AU - Khodarahmi GA AU - Ly TW AU - Valiyev F AU - Leong MK AU - Hakimelahi S AU - Shia KS AU - Chao I TI - Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms JO - Organic and Biomolecular Chemistry VL - 1 IS - 14 SP - 2461 EP - 2467 PY - 2003 ER -

Style

Citing Format

MLA

Hakimelahi GH, et al.. "Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms." Organic and Biomolecular Chemistry, vol. 1, no. 14, 2003, pp. 2461-2467.

APA

Hakimelahi GH, Li PC, Moosavimovahedi AA, Chamani J, Khodarahmi GA, Ly TW, Valiyev F, Leong MK, Hakimelahi S, Shia KS, Chao I (2003). Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms. Organic and Biomolecular Chemistry, 1(14), 2461-2467.

Chicago

Hakimelahi GH, Li PC, Moosavimovahedi AA, Chamani J, Khodarahmi GA, Ly TW, Valiyev F, et al.. "Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms." Organic and Biomolecular Chemistry 1, no. 14 (2003): 2461-2467.

Harvard

Hakimelahi GH et al. (2003) 'Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms', Organic and Biomolecular Chemistry, 1(14), pp. 2461-2467.

Vancouver

Hakimelahi GH, Li PC, Moosavimovahedi AA, Chamani J, Khodarahmi GA, Ly TW, et al.. Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms. Organic and Biomolecular Chemistry. 2003;1(14):2461-2467.

BibTex

@article{ author = {Hakimelahi GH and Li PC and Moosavimovahedi AA and Chamani J and Khodarahmi GA and Ly TW and Valiyev F and Leong MK and Hakimelahi S and Shia KS and Chao I}, title = {Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms}, journal = {Organic and Biomolecular Chemistry}, volume = {1}, number = {14}, pages = {2461-2467}, year = {2003} }

RIS

TY - JOUR
AU - Hakimelahi GH
AU - Li PC
AU - Moosavimovahedi AA
AU - Chamani J
AU - Khodarahmi GA
AU - Ly TW
AU - Valiyev F
AU - Leong MK
AU - Hakimelahi S
AU - Shia KS
AU - Chao I
TI - Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms
JO - Organic and Biomolecular Chemistry
VL - 1
IS - 14
SP - 2461
EP - 2467
PY - 2003
ER -

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