Synthesis of pyrrole urea and pyrrole carbonylurea derivatives

Liu, Meng-Chi; Ong, Chi Wi

doi:10.1016/j.tet.2009.08.003

Cited by 6 publications

(2 citation statements)

References 24 publications

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“…The starting point was the 2-trichloroacetyl-4-nitropyrrole, 1, which has been previously prepared from the trichloroacylation of N-methylpyrrole, followed by nitration. 9 The diazonium salt of pyrrole-2-carboxylic acid 3 was prepared by reduction of the nitro-group of 2, followed by diazotation according to reported procedure. 17 Compound 3 was reacted immediately with pyrrole to give the diazine-pyrrole carboxylic acid product 4.…”

Section: Synthesismentioning

confidence: 99%

“…8 We have been working on modifying the carboxamide bond in distamycin with urea and carbonyl-urea. 9 Photoactive agents are potentially useful as DNA cleaving agents as they are inactive until triggered by irradiation. 10,11 Recent research has focused on the development of photonucleases that damage DNA directly upon irradiation, without requiring the activation of oxygen to form reactive oxygen species.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of directly linked diazine isosteres of pyrrole-polyamide that photochemically cleave DNA

et al. 2012

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A distamycin model containing an isosteric diazine linked pyrrole has been designed and synthesized. The key steps of the synthesis involved the successful diazotization of the 4-amino-pyrrole derivatives to give the diazomium salts, which undergo coupling reactions with N-methylpyrrole to yield the directly linked diazine compounds. The amide isosteric-diazine pyrrole I demonstrated photo-induced DNA damage upon iradiation with UV light (365 nm). Spectrophotometric and mass spectrometric identification suggest that the azo-linkage in I did not dissociate during irradiation. Moreover, compound I produced DNase I footprints with the HexB DNA fragment at AT sites, as well as some other mixed sequences (5'-ATGTCG-3'), indicative of the additional role of the diazine-linkage for interaction at the duplex DNA.

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Section: Synthesismentioning

confidence: 99%