220259-89-2Relevant academic research and scientific papers
Regioselective synthesis of 3,6-disubstituted-2-aminoimidazo[1,2-a]pyridines
Jaramillo, Carlos,Carretero, Juan Carlos,De Diego, J.Eugenio,Del Prado, Miriam,Hamdouchi, Chafiq,Roldán, José Luis,Sánchez-Martínez, Concha
, p. 9051 - 9054 (2007/10/03)
A convenient synthesis of 3,6-disubstituted-2-aminoimidazo[1,2-a]pyridines 3 is described. A halogen-metal exchange study on building block 1 showed that use of i-propyl magnesium chloride is most effective for chemoselective functionalization at position
Anti-viral compounds
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, (2008/06/13)
The present invention relates to compounds of Formula (I) below, which inhibit the growth of picornaviruses, Hepatitus viruses, enteroviruses, cardioviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus. wherein: A is phenyl, pyridyl, substituted phenyl, substituted pyridyl, or benzyl; R is hydrogen, COR4, or COCF3; X is N—OH, O, or CHR1; R1is hydrogen, halo, CN, C1-C4alkyl, —C≡CH, CO(C1-C4alkyl), CO2(C1-C4alkyl), or CONR2R3; R2and R3are independently hydrogen or C1-C4alkyl; A′ is hydrogen, halo, C1-C6alkyl, benzyl, naphthyl, thienyl, furyl, pyridyl, pyrollyl, COR4, S(O)nR4, or a group of the formula R4is C1-C6alkyl, phenyl, or substituted phenyl; n is 0, 1, or 2; R5is independently at each occurrence hydrogen or halo; m is 1, 2, 3, or 4; and R6is hydrogen, halo, CF3, OH, CO2H, NH2, NO2, CONHOCH3, C1-C4alkyl, or CO2(C1-C4alkyl), C1-C4alkoxy; or a pharmaceutically acceptable salt thereof.
2-amino-3-substituted-6-[(E)-1-phenyl-2-(N- methylcarbamoyl)vinyl]imidazo-[1,2-a]pyridines as a novel class of inhibitors of human rhinovirus: Stereospecific synthesis and antiviral activity
Hamdouchi, Chafiq,De Blas, Jesús,Del Prado, Mirian,Gruber, Joseph,Heinz, Beverly A.,Vance, Lori
, p. 50 - 59 (2007/10/03)
A series of 2-amino-3-substituted-6-[(E)-1-phenyl-2-(N- methylcarbamoyl)vinyl]imidazo[1,2-a]-pyridines 1a-i, structurally related to Enviroxime and its analogous benzimidazoles, was designed and prepared for testing as antirhinovirus agents. The imidazo ring in this class of compounds was constructed starting from the aminopyridine after tosylation and subsequent treatment with the appropriate acetamides. The key steps in the synthesis include the development and use of a new Horner-Emmons reagent for the direct incorporation of methyl vinylcarboxamide. The reaction was stereospecific in the substrates 5a-f leading exclusively to the desired E- isomer and avoiding the use of reverse-phase preparative HPLC for the separation of both possible isomers before antiviral activity evaluation. The isopropylsulfonyl group, known as the best substituent at the 1-position in the benzimidazole SAR in terms of activity, was introduced in this new series of imidazo[1,2-a]pyridines via halogen-metal exchange and subsequent treatment with isopropyl isopropanethiolsulfonate. Compounds 1a-i were evaluated in plaque reduction assay and in a cytopathic effect assay. Compounds 1b-d,h exhibited a strong antirhinovirus activity, and no apparent cellular toxicity was visible. The substitution at the 3-position was required for activity. Surprisingly the isopropylsulfonyl in this family of compounds did not enhance the activity as in the case of benzimidazoles. Instead, compound 1i was 4 times less active than its phenyl and sulfide partners. The chemistry as well as the biological evaluation are discussed.
A novel application of the Ullmann coupling reaction for the alkylsulfenylation of 2-amino-imidazo [1,2-a] pyridine
Hamdouchi, Chafiq,De Blas, Jesus,Ezquerra, Jesus
, p. 541 - 548 (2007/10/03)
The Ullmann coupling reaction between the 2-trifluoroacetamido-3-iodo- 6-benzoylimidazo[1,2-a]pyridine and dialkyldisulfides (Me, (i)Pr) mediated by copper bronze in pyridine, resulted in a novel and highly efficient method for the incorporation of alkylt
