ChemInform Abstract: 3‐(2‐Imidazo(4,5‐b)pyridine)propionic Acid and Some of Its Derivatives with Suspected Tuberculostatic Activity.

Bukowski, L.; Janowiec, M

doi:10.1002/chin.198945180

Cited by 10 publications

(10 citation statements)

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“…Imidazopyridine derivatives display anticancer (Lukasik et al, 2012), tuberculostatic (Bukowski & Janowiec, 1989) and antimitotic activities (Aridoss et al, 2006). This study is a continuation of our work (Bourichi et al, 2016;Ouzidan et al, 2010) on the syntheses and structures of new imidazopyridine derivatives.…”

Section: Structure Descriptionmentioning

confidence: 59%

4-Benzyl-6-bromo-2-(4-chlorophenyl)-4H-imidazo[4,5-b]pyridine

et al. 2017

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In the title compound, C19H13BrClN3, the chlorophenyl ring occupies an equatorial position with respect to the mean plane of the imidazopyridine unit, while the other phenyl ring is twisted by 4.1 (2)° with respect to the mean plane of the imidazopyridine unit. In the crystal, pairwise C—H...Br interactions link the molecules into dimers, forming anR22(16) ring motif. In addition, weak π–π stacking interactions stabilize the crystal packing.

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Section: Structure Descriptionmentioning

confidence: 59%

4-Benzyl-6-bromo-2-(4-chlorophenyl)-4H-imidazo[4,5-b]pyridine

et al. 2017

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“…For example, they are known for their anticancer activity (Dash et al, 2008) and antibacterial (Capelli et al, 2006), antimitotic (Temple, 1990) and tuberculostatic (Bukowski & Janowiec, 1989) properties. In a previous study, we reported the synthesis of ethyl 2-(6-bromo-2-phenyl-1H-imidazo [4,5-b]-pyridin-1-yl)acetate (Hjouji et al, 2016).…”

Section: Structure Descriptionmentioning

confidence: 99%

Ethyl 2-(6-bromo-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)acetate

Hjouji¹,

Mague

Rodi³

et al. 2016

IUCr Data

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The title imidazo [4,5-b] pyridine derivative, C 16 H 14 BrN 3 O 2 , crystallizes with two independent molecules (1 and 2) in the asymmetric unit. In molecule 1, the pendant phenyl ring is inclined to the imidazo [4,5-b]pyridine core by 43.10 (4) while in molecule 2 the corresponding angle is 49.43 (4) . The two molecules differ primarily in the conformations of the ester substituents. In the crystal, molecules are linked via C-HÁ Á ÁN and C-HÁ Á ÁO hydrogen bonds, forming sheets parallel to the ab plane. Structure descriptionImidazo [4,5-b]pyridines are an important class of heterocyclic rings, considered as analogue of purine, widely studied owing to their broad biological activities. For example, they are known for their anticancer activity (Dash et al., 2008) and antibacterial (Capelli et al., 2006), antimitotic (Temple, 1990) and tuberculostatic (Bukowski & Janowiec, 1989) properties. In a previous study, we reported the synthesis of ethyl 2-(6-bromo-2-phenyl-1H-imidazo[4,5-b]-pyridin-1-yl)acetate (Hjouji et al., 2016). The present study is extended to the synthesis of the ethyl 2-(6-bromo-2-phenyl-3H-imidazo [4,5-b]pyridin-3-yl)acetate regioisomer, by the action of ethyl 2-bromoacetate on 6-bromo-2-phenyl-3H-imidazo [4,5-b]pyridine under the same conditions.The asymmetric unit of the title compound, contains two independent molecules (1 and 2), which differ primarily in the conformations of the ester substituents ( Figs. 1 and 2). The bicyclic imidazo [4,5-b]pyridine core of molecule 1 is planar to within 0.012 (1) Å , while that in molecule 2 is planar to within 0.020 (1) Å . In molecule 1, the pendant phenyl

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“…The most commonly used method for synthesis of 3‐heteryl‐2‐iminocoumarins is the Knoevenagel condensation of salicylic aldehydes with nitriles of heterylacetic acids [27–30]. However, for synthesis of 3‐(4‐oxo‐3,4‐dihydrothieno[2,3‐ d ]pyrimidin‐2‐yl)‐2‐iminocoumarins this approach is not convenient enough due to the difficulties in the starting building‐blocks, the corresponding 2‐(4‐oxo‐3,4‐dihydrothieno[2,3‐ d ]pyrimidin‐2‐yl)acetonitriles, preparation [31].…”

Section: Introductionmentioning

confidence: 99%

Convenient synthesis of substituted 2‐(2‐iminocoumarin‐3‐yl)thieno[2,3‐d]pyrimidin‐4‐ones

Shynkarenko¹,

Vlasov²,

Kovalenko³

et al. 2010

Journal of Heterocyclic Chem

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magnified image The interaction of both 2‐iminocoumarin‐3‐carbonitriles and 2‐iminocoumarin‐3‐carbothioamides with 2‐aminothiophen‐3‐carboxamides lead to formation of 3‐(4‐oxo‐3,4‐dihydrothieno[2,3‐d]pyrimidin‐2‐yl)‐2‐iminocoumarins in two steps. The simplicity of the procedure, as well as the high yields of the target products make this method to be a good alternative of Knoevenagel condensation for the synthesis of 3‐(4‐oxo‐3,4‐dihydrothieno[2,3‐d]pyrimidin‐2‐yl)‐2‐iminocoumarins. J. Heterocyclic Chem., (2010).

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ChemInform Abstract: 3‐(2‐Imidazo(4,5‐b)pyridine)propionic Acid and Some of Its Derivatives with Suspected Tuberculostatic Activity.

Cited by 10 publications

References 0 publications

4-Benzyl-6-bromo-2-(4-chlorophenyl)-4H-imidazo[4,5-b]pyridine

4-Benzyl-6-bromo-2-(4-chlorophenyl)-4H-imidazo[4,5-b]pyridine

Ethyl 2-(6-bromo-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)acetate

Convenient synthesis of substituted 2‐(2‐iminocoumarin‐3‐yl)thieno[2,3‐d]pyrimidin‐4‐ones

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