Synthesis and antitubercular activity of novel 4-substituted imidazolyl-2,6-dimethyl-N3,N5-bisaryl-1,4-dihydropyridine-3,5-dicarboxamides

Fassihi, Afshin; Azadpour, Zahra; Delbari, Neda; Saghaie, Lotfollah; Memarian, Hamid Reza; Sabet, Razieh; Alborzi, Abdolvahab; Miri, Ramin; Pourabbas, Bahman; Mardaneh, Jalal; Mousavi, Pegah; Moeinifard, Behzad; Sadeghi‐Aliabadi, Hojjat

doi:10.1016/j.ejmech.2009.03.027

Cited by 63 publications

(36 citation statements)

References 24 publications

(27 reference statements)

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“…In contrary to this, the reports on DHP carboxamide derivatives are meager [12]. However, recently, the synthesis and antitubercular activity of new N,N-diaryl-3,5-dicarbamoyl derivatives of 1,4-DHPs and 1,4-DHPs containing different ester substitutes and diethyl carbamoyl groups have been reported [13]. It is also of interest to incorporate some biologically potent heterocycles viz., pyridine [14], quinazolin-4(3H)-one [15], imidazole [16], thiophene [17], furan [18], and pyrrole [19] into the DHP system along with the carboxamide functionality with a regard to obtaining an increased biological potency.…”

Section: Introductionmentioning

confidence: 94%

Facile Synthesis and Antibacterial, Antitubercular, and Anticancer Activities of Novel 1,4‐Dihydropyridines

Sirisha

Garlapati

Reddy³

2010

Archiv der Pharmazie

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A series of twenty new 4-substituted-2,6-dimethyl-3,5-bis-N-(heteroaryl)-carbamoyl-1,4-dihydropyridines have been prepared from a three-component one-pot condensation reaction of N-heteroaryl acetoacetamide, an aromatic/heteroaromatic aldehyde, and ammonium acetate under four different experimental conditions. Except for the conventional method, all the experimental conditions were simple, eco-friendly, economical, and the reactions were rapid and high-yielding. The methods employed have been compared in terms of yields, cost, and simplicity. The synthesized compounds were characterized by different spectroscopic techniques and evaluated for their in-vitro anticancer, antibacterial, and antitubercular activities. Amongst the compounds tested, compound 25 exhibited the highest anticancer activity while compounds 14 and 18 exhibited significant antibacterial and antitubercular activities.

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Section: Introductionmentioning

confidence: 94%

Facile Synthesis and Antibacterial, Antitubercular, and Anticancer Activities of Novel 1,4‐Dihydropyridines

Sirisha

Garlapati

Reddy³

2010

Archiv der Pharmazie

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“…Another series of pyridine derivatives were developed by Fassihi et al who synthesized compound 54 (figure 17), a potent anti-TB agent with activity similar to RIF. The results of these compounds showed that an imidazole group as a substituent is equivalent to a nitro phenyl group, which has been reported in anti-TB agents derived from 1,4-dihydropyridinecarboxamides (Fassihi et al, 2009). Another important heterocyclic for the design of anti-TB agents is the pyridazine moiety.…”

Section: Nitrogen Heterocyclic Derivativesmentioning

confidence: 82%

Antitubercular Drugs Development: Recent Advances in Selected Therapeutic Targets and Rational Drug Design

Bocanegra-García¹,

García²,

Palma-Nicolás³

et al. 2011

Drug Development - A Case Study Based Insight Into Modern Strategies

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“…A series of derivatives showed that if the pyrimidine ring is substituted in any position or changed by an isosteric, this decreases anti--TB activity. Amino group substitutions by phthalimide ring also lead to a decrease anti--TB activity (32). Modifications in the pyridine ring decrease anti--TB activity.…”

Section: Other Non--nitrogen Heterocyclic Derivativesmentioning

confidence: 99%

“…The results showed that an imidazole group as a substituent is equivalent to a nitro phenyl group, which has been reported in anti--TB agents derived from 1,4--dihydropyridinecarboxamides. 32 Another important heterocyclic for the design of anti--TB compounds is a pyridazine moiety. In these compounds a relationship between Br, Cl and CH3 substituents, respectively, with Br and vinyl has been found with a favorable anti--TB activity.…”

Section: Nitrogen Heterocyclic Derivativesmentioning

confidence: 99%

Antitubercular drugs: advances in nitrogen containing heterocyclic compounds and some other derivatives

Asif

2014

J PHARM CHEM

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Tuberculosis (TB) caused by Mycobacterium tuberculosis is an infectious disease. Control of TB is complicated by difficulties in the long--course chemotherapy treatment, the inability to eliminate latent microbes, and the increasing emergence of Multidrug Resistant (MDR) strains of M. tuberculosis. New anti--TB drugs are urgently needed, including developments of short--term treatments to minimize the emergence of drug resistance and new drugs to treat multidrug resistant tuberculosis and to eliminate the latent microbes. Many new structural anti--TB agents exhibited promising activities against susceptible and resistant strains of M. tuberculosis. The diarylquinoline with superior anti--tuberculotic activity and encouraging results of nitroimidazopyrans and oxazolidinones have generated considerable excitement.

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Synthesis and antitubercular activity of novel 4-substituted imidazolyl-2,6-dimethyl-N3,N5-bisaryl-1,4-dihydropyridine-3,5-dicarboxamides

Cited by 63 publications

References 24 publications

Facile Synthesis and Antibacterial, Antitubercular, and Anticancer Activities of Novel 1,4‐Dihydropyridines

Facile Synthesis and Antibacterial, Antitubercular, and Anticancer Activities of Novel 1,4‐Dihydropyridines

Antitubercular Drugs Development: Recent Advances in Selected Therapeutic Targets and Rational Drug Design

Antitubercular drugs: advances in nitrogen containing heterocyclic compounds and some other derivatives

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