Contribution à l'étude du nitrile et de l'aldéhyde 3,4‐dinitro‐benzoïques

Goldstein, Henri; Voegeli, Roland

doi:10.1002/hlca.19430260413

Cited by 10 publications

(2 citation statements)

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“…The amino acid esters (8-10) could be synthesized from the common diami- nophenyl intermediate 28 (Scheme 3). 3,4-Dinitrobenzoic acid 24 was converted to its aldehyde 25 20 by sequential reactions with BH 3 •THF 21 and PCC. 22 The reaction of aldehyde 25 with ylide 4 afforded the pure (Z)-isomer enamide 26 in 77% yield after crystallization from EtOAc and flash chromatography on silica gel using CH 2 Cl 2 as eluent.…”

Section: Resultsmentioning

confidence: 99%

Catalytic Asymmetric Syntheses of Tyrosine Surrogates

et al. 2008

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Section: Resultsmentioning

confidence: 99%

Catalytic Asymmetric Syntheses of Tyrosine Surrogates

et al. 2008

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“…The synthetic approach used for the preparation of 2‘‘-substituted derivatives of 5-phenylterbenzimidazole is outlined in Scheme . Reaction of 4-phenyl-1,2-phenylenediamine 12 ( 21 ) with 3,4-dinitrobenzaldehyde ( 22 ) resulted in the formation of 2-(3,4-dinitrophenyl)-5-phenylbenzimidazole ( 23 ) in 66% yield. Catalytic hydrogenation of 23 followed by reaction of the resulting crude diamine with 22 provided 5-phenyl-2-[2‘-(3,4-dinitrophenyl)benzimidazol-5‘-yl]benzimidazole ( 24 ) in 94% yield.…”

Section: Chemistrymentioning

confidence: 99%

Terbenzimidazoles: Influence of 2‘‘-, 4-, and 5-Substituents on Cytotoxicity and Relative Potency as Topoisomerase I Poisons

Kim

Liu

et al. 1997

J. Med. Chem.

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Terbenzimidazoles poison the nuclear enzyme topoisomerase I and possess significant cytotoxic activity against several human tumor cell lines. The relative pharmacological activity of 4,5- and 5,6-benzoterbenzimidazoles was compared to that of 5-phenylterbenzimidazole (3). 5,6-Benzoterbenzimidazole is inactive as a topoisomerase I poison and did not exhibit significant cytotoxic activity. In contrast, 4,5-benzoterbenzimidazole retained activity as a topoisomerase I poison but exhibited weak cytotoxic activity relative to 3. While 5-(1-naphthyl)terbenzimidazole is less potent than 3 as a topoisomerase I poison and cytotoxic agent, 5-(2-naphthyl)-terbenzimidazole has comparable activity to 3. The presence of a p-methoxy or p-chloro substituent on the phenyl moiety did not dramatically alter the pharmacological activity of 3. Several analogs of 3 were synthesized wherein the 2"-substituent varied from methyl, ethyl, propyl, isopropyl, phenyl to p-methoxyphenyl. Evaluation of the intrinsic activity of these analogs as topoisomerase I poisons indicates that topoisomerase I poisoning was not diminished by the presence of a methyl, ethyl, propyl, and isopropyl substituent at the 2"-position. Among the various 2"-substituted analogs evaluated, only in the case of 2"-(p-methoxyphenyl)-5-phenylterbenzimidazole was a significant decrease in cytotoxicity observed.

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Thionyl Chloride

Wirth¹

2001

Encyclopedia of Reagents for Organic Synthesis

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Contribution à l'étude du nitrile et de l'aldéhyde 3,4‐dinitro‐benzoïques

Cited by 10 publications

References 1 publication

Catalytic Asymmetric Syntheses of Tyrosine Surrogates

Catalytic Asymmetric Syntheses of Tyrosine Surrogates

Terbenzimidazoles: Influence of 2‘‘-, 4-, and 5-Substituents on Cytotoxicity and Relative Potency as Topoisomerase I Poisons

Thionyl Chloride

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