Synthèse, structure et activité cytostatique d'une série de périmidines substitués en 2

Braña, Miguel F.; Garrido, María Concepción Domínguez; López-Rodrı́guez, Marı́a L.; Morcillo, M. J.; Alvarez, Y.; Valladares, Y.; Klebe, G.

doi:10.1016/0223-5234(90)90203-f

Cited by 11 publications

(1 citation statement)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…They have been used as anti-ulcer, anti-microbial, and anti-fungal agents [11,12]. Perimidines have also been described as DNA-intercalating and anti-tumor agents against several carcinogenic cell lines [13,14,15,16]. Very recently, we reported some perimidine anti-tumor agents that showed good activity against the MCF-7 breast cancer cell line and HEPG-2 liver cancer cell line [17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

et al. 2014

View full text Add to dashboard Cite

Two series of naphtho[1,8-ef][1,4]diazepines and pyrrolo[1,2-a]perimidines were prepared starting from 1,8-diaminonaphthalene and hydrazonoyl chlorides. The structures of the products were determined on the basis of their spectral data and elemental analyses. The mechanism of formation of such products was also discussed. The prepared compounds were screened for their antitumor activity against three cell lines, namely, MCF-7, TK-10 and UACC-62, and some derivatives showed promising activity.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

et al. 2014

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: Synthesis, Structure and Cytostatic Activity of a Series of 2‐Substituted Perimidines.

et al. 1990

View full text Add to dashboard Cite

show abstract

Iminophosphorane‐Mediated Synthesis of Fused Perimidines: Preparation of Quinazolino[3,4‐a]perimidine Derivatives

et al. 1994

View full text Add to dashboard Cite

An aza-Wittig-type reaction of iminophosphoranes 2 and 3, derived from 2-(2-azidophenyl)-l,2-dihydroperimidine and 2-(2-azidophenyl)perimidine, respectively, with isocyanates, carbon dioxide, carbon disulfide and acyl chlorides provides 6-substituted quinazolino[3,4-a]perimidines 4-10.The heteroaromatic system perimidine exhibits simultaneously the distinct properties of compounds with an excess and a deficiency of K electrons, together with a wide variety of practical applications [']. In spite of the extensive work spent on the preparation of perimidine derivatives, only a few methods of the synthesis of fused perimidines, namely quinazolino[3,4-~]perimidines have been reported until now. It has only been briefly mentioned that treatment of 2-(2-aminophenyl)perimidine with either chlorothioformyl chloride ['] or aromatic aldehydes and further oxidationl3] provide quinazolin0[3,4-~]perimidines. Reaction of 2-isocyanatobenzoyl chloride with 1,s-diaminonaphthalene affords 5H-6-oxoquinazolino[3,4-u]perimidine in moderate yieldL4]. The main disadvantage of these methods is that the scope for the introduction of different substituents is limited. We now report on a general synthesis of functionalized quinazolin0[3,4-~]perimidines which is capable of modification to allow the introduction of a wide range of substituents. Our approach is based on an efficient application of the aza-Wittigheterocumulene-mediated annulation strategy involving the NH group of the perimidine ring. Although a wide variety of nitrogen-containing heterocycles have been prepared by means of this methodol0gy~~1, no examples involving pyrimidinelike amino groups have been reported.The Staudinger reaction of 1,2-dihydroproperimidine 1, readily available in 78% yield by condensation of 1,s-diaminonaphtalene with o-azidobenzaldehyde [6], with triphenylphosphane at room temperature provides the iminophosphorane 2 in 87% yield, which undergoes dehydrogenation by the action of 10% P d C to give the iminophosphorane 3 in 80% yield (Scheme 1).An aza-Wittig-type reaction of iminophosphorane 2 with aromatic isocyanates in dry dichloromethane at reflux temperature directly affords 6-arylamino-14,14a-dihydroquinazolino[3,4-u]perimidines 4 in moderate yields (45-51%). Likewise, reaction with carbon dioxide or carbon disulfide in a sealed tube at 100°C provides the 6-0x0 or 6-thioxo derivatives 5 and 6, respectively, in good yields (Scheme 2).On the other hand, iminophosphorane 3 reacts with aromatic and aliphatic isocyanates in dichloromethane at room temperature to give 6-alkyl(aryl)aminoquinazolino[3,4-u]perimidines 8 in good yields, while iminophosphorane 3 does not react with aroyl chlorides in the presence of triethylamine in toluene at reflux tempera-

show abstract

Synthèse, structure et activité cytostatique d'une série de périmidines substitués en 2

Cited by 11 publications

References 8 publications

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

ChemInform Abstract: Synthesis, Structure and Cytostatic Activity of a Series of 2‐Substituted Perimidines.

Iminophosphorane‐Mediated Synthesis of Fused Perimidines: Preparation of Quinazolino[3,4‐a]perimidine Derivatives

Contact Info

Product

Resources

About