Discovery and structure–activity relationship of thienopyridine derivatives as bone anabolic agents

Saito, Keiji; Nakao, Akira; Shinozuka, Tsuyoshi; Shimada, Kousei; Matsui, Satoshi; Oizumi, Kiyoshi; Yano, Kouji; Ohata, Keiko; Nakai, Daisuke; Nagai, Yoko; Naito, Satoru

doi:10.1016/j.bmc.2013.01.071

Cited by 33 publications

(22 citation statements)

References 27 publications

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“…The thieno [2,3-b]pyridine derivatives occupy special place and have attracted considerable attention because of their broad pharmacological activities, including anticancer [1][2][3][4][5][6][7][8][9], antiviral [10][11][12][13], anti-inflammatory [14][15][16][17], antimicrobial [18,19], antidiabetic [20][21][22][23], antihypertensive [24][25][26] and osteogenic [27,28] activities, in addition to treatment of CNS disorders [29][30][31].…”

Section: Introductionmentioning

confidence: 99%

Utility of thieno[2,3-b] pyridine derivatives in the synthesis of some condensed heterocyclic compounds with expected biological activity

Hassan¹,

Sarg²,

Said³

et al. 2013

Univers Org Chem

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Section: Introductionmentioning

confidence: 99%

Utility of thieno[2,3-b] pyridine derivatives in the synthesis of some condensed heterocyclic compounds with expected biological activity

Hassan¹,

Sarg²,

Said³

et al. 2013

Univers Org Chem

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“…Then, the obtained imine compounds ( 129 ) was reacted with solution of NaOH (1 M) for 30 minutes. The condensation was performed by base treatment of the intermediate product and the novel compounds ( 130 ) containing a pyridine ring was formed [41] . (Scheme 19).…”

Section: Formation Of Heterocycle Structures By Dmf‐dma Reactionsmentioning

confidence: 99%

Enamines and Dimethylamino Imines as Building Blocks in Heterocyclic Synthesis: Reactions of DMF‐DMA Reagent with Different Functional Groups

Gümüş

Koca

2020

ChemistrySelect

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N,N‐Dimethylformamide dimethyl acetal (DMF‐DMA) reagent can react with different functional groups of organic compounds. Enamines and dimethylamino imines are obtained, when the DMF‐DMA reagent is reacted with methylene, methyl and amino groups. These products are formed in the intermediate step in the synthesis of many hetero rings. These compounds are especially used as a starting material in the synthesis of heterostructures such as pyrimidine, pyridine, pyrazole, etc. Therefore, DMF‐DMA has been particularly prominent as a reagent in targeted synthesis and designs of many heterocyclic compounds. Herein, the reactions of DMF‐DMA reagent with different functional groups are categorized in four classes (methylene, methyl, amino, other groups) and the reactions of obtained enamine and dimethylamino imine compounds are investigated in detail such as nucleophilic addition, intramolecular cyclization or condensation reactions. The synthesis and continuation reactions of the enamine and dimethylamino imine compounds are also examined in terms of experimental conditions and reagents used.

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“…On the other hand, many reports have documented the important biological activities of thieno[2,3- b ]pyridine derivatives in anticancer [ 19 , 20 , 21 ], antimicrobial [ 22 , 23 ], antiviral [ 24 , 25 ], anti-inflammatory [ 26 ] and osteogenic [ 27 ] activities. As a result, thieno[2,3- b ]pyridine compounds and their fused derivatives with the bioactive pyrimidine ring [ 28 , 29 ] have attracted great interest in the last decade; several pyrido[3’,2’:4,5]thieno[3,2- d ]pyrimidine derivatives were synthesized and gave significant pharmacological properties as antimicrobial [ 30 , 31 , 32 ], anticancer [ 33 , 34 ] and protein kinase inhibitors [ 35 , 36 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of New Pyridothienopyrimidine Derivatives as Antibacterial Agents and Escherichia coli Topoisomerase II Inhibitors

et al. 2020

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The growing resistance of bacteria to many antibiotics that have been in use for several decades has generated the need to discover new antibacterial agents with structural features qualifying them to overcome the resistance mechanisms. Thus, novel pyridothienopyrimidine derivatives (2a,b–a,b) were synthesized by a series of various reactions, starting with 3-aminothieno[2,3-b]pyridine-2-carboxamides (1a,b). Condensation of compounds 1a,b with cyclohexanone gave 1’H-spiro[cyclohexane-1,2’-pyrido[3’,2’:4,5]thieno[3,2-d]pyrimidin]-4’(3’H)-ones (2a,b), which in turn were utilized to afford the target 4-substituted derivatives (3a,b–8a,b). In vitro antibacterial activity evaluations of all the new compounds (2a,b–8a,b) were performed against six strains of Gram-negative and Gram-positive bacteria. The target compounds showed significant antibacterial activity, especially against Gram-negative strains. Moreover, the compounds (2a,b; 3a,b; 4a,b; and 5a,b) that exhibited potent activity against Escherichia coli were selected to screen their inhibitory activity against Escherichia coli topoisomerase II (DNA gyrase and topoisomerase IV) enzymes. Compounds 4a and 4b showed potent dual inhibition of the two enzymes with IC50 values of 3.44 µΜ and 5.77 µΜ against DNA gyrase and 14.46 µΜ and 14.89 µΜ against topoisomerase IV, respectively. In addition, docking studies were carried out to give insight into the binding mode of the tested compounds within the E. coli DNA gyrase B active site compared with novobiocin.

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Discovery and structure–activity relationship of thienopyridine derivatives as bone anabolic agents

Cited by 33 publications

References 27 publications

Utility of thieno[2,3-b] pyridine derivatives in the synthesis of some condensed heterocyclic compounds with expected biological activity

Utility of thieno[2,3-b] pyridine derivatives in the synthesis of some condensed heterocyclic compounds with expected biological activity

Enamines and Dimethylamino Imines as Building Blocks in Heterocyclic Synthesis: Reactions of DMF‐DMA Reagent with Different Functional Groups

Synthesis and Biological Evaluation of New Pyridothienopyrimidine Derivatives as Antibacterial Agents and Escherichia coli Topoisomerase II Inhibitors

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