ChemInform Abstract: Antimycobacterial Activity of New ortho‐, meta‐, and para‐Toluidine Derivatives.

Biava, Mariangela; Fioravanti, Rossella; Porretta, Giulio Cesare; Sleiter, G.; Deidda, Delia; Lampis, Giorgio; Pompei, Raffaello

doi:10.1002/chin.200012263

Cited by 2 publications

(3 citation statements)

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“…There is one other mention in the literature of alkylating the nitrogen of a 2,5‐disubstituted pyrrole . When tested against Mycobacterium tuberculosis and Herpes simplex 2 (HSV2), compound 24 exhibited a very good activity . Compounds 25 to 27 reported here are new and warrant testing for antimicrobial and antiviral activity.…”

Section: Resultsmentioning

confidence: 99%

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A new synthesis of biologically active pyrroles: Formal synthesis of pentabromopseudilin, bimetopyrol, and several antitubercular agents

Karimi

et al. 2019

Journal of Heterocyclic Chem

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Although pyrroles have been synthesized from azido dienes, the corresponding reactions of structurally similar nitrodienes had not been investigated until it became the main focus of this study. This article describes the synthesis of several biologically active pyrroles and mechanistically intriguing results in connection with our new approach using nitrodienes in the presence of Ph 3 P and a Mo catalyst, bis (acetylaceto)dioxomolybdenum (VI). The final precursor of pentabromopseudilin (PBP), pseudilin, was synthesized in four steps from ohydroxycinnamaldehyde. An alternate pathway to PBP proceeded through omethylpseudilin, prepared in two steps from o-methoxycinnamaldehyde. Both starting materials are commercially available. Similarly, bimetopyrol (2methyl-4,5-bis(p-methoxyphenyl)pyrrole), a potent anti-inflammatory, was prepared using the new methodology. The remarkable conversion of nitrodienes 14 and 15 to bimetopyrol highlights the formation of a nitroso or nitrene intermediate. We also established that 14 and 15 interconvert in the presence of ambient light and each converts to bimetopyrol when reacted separately. The wide application of our synthetic methodology includes preparation of several antitubercular and Herpes Simplex 2 (HSV2) agents.

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Section: Resultsmentioning

confidence: 99%

“…The syntheses of pentabromopseudilin (PBP), bimetopyrol (BMP), and antitubercular agents have attracted the attention of chemists for a number of years. The antibacterial properties of PBP and the anti‐inflammatory effect of BMP are well documented.…”

Section: Introductionmentioning

confidence: 99%

A new synthesis of biologically active pyrroles: Formal synthesis of pentabromopseudilin, bimetopyrol, and several antitubercular agents

Karimi

et al. 2019

Journal of Heterocyclic Chem

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show abstract

“…The synthesis and antimycobacterial efficacy of a new class of styryl derivatives (74a-c) were reported (Scheme 11) (Biava et al, 1997). The desired styryl derivatives (74a-c) were prepared in a three-steps sequence that begins by the reduction of the starting nitro compounds (71a-c) furnishing ortho-, meta-or para-aminotoluidines possessing either an imidazole, pyrazine or morpholine frame (72a-c).…”

Section: Cinnamaldehyde-derived Hydrazonesmentioning

confidence: 99%