Novel halogenated 1,4-dihydropyridines: Synthesis, bioassay, microsomal oxidation and structure-activity relationships

Hernández-Gallegos, Zurisaddai; Hong, Enrique; Posadas, F; Hernández-Gallegos, E

doi:10.1016/0223-5234(96)88245-6

Cited by 13 publications

(8 citation statements)

References 29 publications

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“…The formation of compounds 8 and 9 can be rationalized asexplained by an in situ intramolecular oxidation-reduction reaction of compound 2 (Scheme 4), since because it is well known that the dihydropyridine moiety comport oneselfbehaves as a reductive system [10,11,12] and the nitrophenyl framework could acts as an oxiddizingant agent [13]. We presume that one of the first steps could be the formation of the N-OH intermediates you 15 and subsequent cyclization gives compound 8 .…”

Section: Results Aand Discussionmentioning

confidence: 99%

Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction

et al. 2001

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The reaction of 5-hydroxy-2-nitrobenzaldehyde with ethyl acetoacetate in ammonia gave the two expected isomeric 1,4- and 1,2-dihydropyridines resulting from the normal Hantzsch reaction. However, the combination of 2-nitrobenzaldehyde with ethyl acetoacetate under the same conditions yielded four products: the two normal isomeric dihydropyridines and two tricyclic compounds. When we attempted to independently synthesize the two tricyclic compounds by reductive cyclization of 4-(2-nitrophenyl)-2,6-dimethyl-3,5-dicarbetoxy-1,4-dihydropyridine and 2-(2-nitrophenyl)-4,6-dimethyl-3,5-dicarbetoxy-1,2-dihydropyridine with tin (II) chloride in hydrochloric acid media, we obtained instead an indole and a quinoline derivative, respectively.

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Section: Results Aand Discussionmentioning

confidence: 99%

Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction

et al. 2001

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“…The calculations were made by an FW/FB computer program, which has been used previously in this kind of analysis. 12,13 For the FW/FB analyses, all the 28 compounds were included by supposing that both agonists and antagonists are interacting with the receptor by a similar binding mode. The compound (−)6 was chosen as the reference compound for all the analyses.…”

Section: Free-wilson Methodsmentioning

confidence: 99%

A quantitation of stereoselectivity by the Free-Wilson method

Hernández-Gallegos

Lehmann

1999

Chirality

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“…− Acridine derivative have the great importance in biological activities like anti‐malarial,− anti‐bacterial, anti‐inflammatory etc . Further, these derivatives also found applications in industries and production of dyes …”

Section: Introductionmentioning

confidence: 99%

A Facile L‐Proline Catalyzed One‐Pot Synthesis of Xanthene and Acridine Based Quinolones via Knoevenagel Condensation Reaction

Reddy

Sivaramakrishna

2020

ChemistrySelect

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A highly efficient, three-component one-pot and L-proline catalyzed Knoevenagel condensation reaction of substituted-2phenoxyquinoline-3-carbaldehyde, 1,3-cyclohexanedione/dimedone or ammonium acetate is described. These reactions afford unexpected products of xanthene and acridine based quinolones in ethanol with good yields. All these isolated products are characterised by spectroscopic and analytical data.[a] M.

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Novel halogenated 1,4-dihydropyridines: Synthesis, bioassay, microsomal oxidation and structure-activity relationships

Cited by 13 publications

References 29 publications

Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction

Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction

A quantitation of stereoselectivity by the Free-Wilson method

A Facile L‐Proline Catalyzed One‐Pot Synthesis of Xanthene and Acridine Based Quinolones via Knoevenagel Condensation Reaction

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