4-Hydroxy-2-quinolones 7. Synthesis and biological properties of 1-R-3-(2-benzimidazolyl)-4-hydroxy-2-quinolones

Украинец, И. В.; Bezuglyi, P. A.; Gorokhova, O. V.; Treskach, V. I.; Туров, А. В.

doi:10.1007/bf00528643

Cited by 3 publications

(4 citation statements)

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“…N - o -Phenylamino-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide (9). Compound 9 was prepared from quinolinone 3 and 1,2-phenylenediamine, according to Method B: yield 65%, light green solid, mp 230−232 °C (lit . mp 230−232 °C).…”

Section: Methodsmentioning

confidence: 99%

“…Compound 9 was prepared from quinolinone 3 and 1,2-phenylenediamine, according to Method B: yield 65%, light green solid, mp 230-232 °C (lit. 60 mp 230-232 °C). 1 H NMR (CDCl 3 ): δ 16.61 (s, 1H, OH), 12.17 (s, 1H, CONH), 8.26 (dd, 1H, J 5,6 ) 8.1, J 5,7 ) 1.5 Hz, 5-H), 7.73 (dtd, 1H, J 7,8 ) 8.7 Hz, J 7,6 ) 6.9 Hz, J 7,5 ) 1.5 Hz, 7-H), 7.55 (dd, 1H, J ) 8.4, 1.8 Hz), 7.09 (ddd, 1H, J ) 9.3, 7.8, 1.5 Hz), 6.85 (pseudotriplet, 2H), 7.41 (d, J 8,7 ) 9.0 Hz, 1H, 8-H), 7.35 (ddd, 1H, J 6,5 ) 8.1 Hz, J 6,7 ) 7.2 Hz, J 6,8 ) 1.2 Hz, 6-H), 3.93 (br s, 2H, -NH 2 ), 3.75 (s, 3H, 3 ).…”

Section: N-o-phenylamino-12-dihydro-4-hydroxy-1-methyl-2-oxo-3quinoli...mentioning

confidence: 99%

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Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents

et al. 2007

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A series of N-substituted-quinolinone-3-aminoamides and their hybrids containing the alpha-lipoic acid functionality were designed and synthesized as potential bifunctional agents combining antioxidant and anti-inflammatory activity. The new compounds were evaluated for their antioxidant activity and for their ability to inhibit in vitro lipoxygenase as well as for their anti-inflammatory activity in vivo. In general, the derivatives were found to be potent antioxidant or anti-inflammatory agents. The results are discussed in terms of structure-activity relationships and an attempt is made to define the structural features required for activity.

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Section: Methodsmentioning

confidence: 99%

Section: N-o-phenylamino-12-dihydro-4-hydroxy-1-methyl-2-oxo-3quinoli...mentioning

confidence: 99%

Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents

et al. 2007

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“…The initial method involved the reaction of anthranilic acid esters ( 6a and 6b ) with methyl malonyl chloride. The products ( 7a and 7b ) were then condensed with phenylenediamine at elevated temperatures in the absence of solvent − to yield the 4-hydroxy-3-benzimidazol-2-ylhydroquinolin-2-ones ( 8a and 8b ) in low to moderate yields (Scheme , a). The synthesis of 8c started from anthranilonitrile and used the same conditions as for the preparation of 8a and 8b to yield the 4- amino -3-benzimidazol-2-ylhydroquinolin-2-one 8c in poor yield (Scheme , a).…”

Section: Chemistrymentioning

confidence: 99%

Design, Structure−Activity Relationships and in Vivo Characterization of 4-Amino-3-benzimidazol-2-ylhydroquinolin-2-ones: A Novel Class of Receptor Tyrosine Kinase Inhibitors

Renhowe¹,

Pecchi²,

Shafer³

et al. 2008

J. Med. Chem.

129

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The inhibition of key receptor tyrosine kinases (RTKs) that are implicated in tumor vasculature formation and maintenance, as well as tumor progression and metastasis, has been a major focus in oncology research over the last several years. Many potent small molecule inhibitors of vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor (PDGFR) kinases have been evaluated. More recently, compounds that act through the complex inhibition of multiple kinase targets have been reported and may exhibit improved clinical efficacy. We report herein a series of potent, orally efficacious 4-amino-3-benzimidazol-2-ylhydroquinolin-2-one analogues as inhibitors of VEGF, PDGF, and fibroblast growth factor (FGF) receptor tyrosine kinases. Compounds in this class, such as 5 (TKI258), are reversible ATP-competitive inhibitors of VEGFR-2, FGFR-1, and PDGFRbeta with IC(50) values <0.1 microM. On the basis of its favorable in vitro and in vivo properties, compound 5 was selected for clinical evaluation and is currently in phase I clinical trials.

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“…This behavior is attributed specifically to the carbamide bridge connecting the two heterocyclic fragments. For comparison, such anomalies are not found in the absence of this bridge [16,24] or when it is replaced by a methylene or ethylene unit [20].…”

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confidence: 99%

4-hydroxy-2-quinolones. 191.* synthesis, tautomerism and biological activity of benzimidazol-2-ylamides of 1-r-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids

Украинец

Grinevich

Ткач

et al. 2011

Chem Heterocycl Comp

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A series of benzimidazol-2-ylamides of 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids was prepared in a search for biologically active compounds. These compounds exist in the crystal exclusively in the amide form, while in solution amide↔imide tautomerism is observed. The results of a study of the antithyroid and antituberculosis activities of these compounds are given.It has recently been noticed more frequently that many autoimmune and other human diseases such as rheumatoid arthritis [2], lupus [3], Sjögren's syndrome [4], myasthenia [5], kidney disease [6], cancer [7], and tuberculosis [ 8] are accompanied by hyperfunction of the thyroid gland. Thus, after diagnosis of such diseases, it is strongly recommended to check periodically the thyroid hormone level so that, when necessary, the therapy can be properly modified. Furthermore, the current arsenal of antithyroid drugs available to the physicians is very limited. The present drugs have serious side effects and, as a consequence, many contraindications for practical application [9][10][11][12][13][14][15]. For this reason, the search for new safe drugs suitable for treating hyperthyroidotoxicosis holds considerable importance today.Compounds with high antithyroid activity, low toxicity, and no goiter-inducing effect were discovered in a study of the biological properties of 3-(benzimidazol-2-yl)-4-hydroxy-2-oxo-1,2-dihydroquinolines [16] and then their many structural analogs [17][18][19][20]. As a result, a new drug has been developed on the basis of one of them for treating diseases related to overproduction of thyroid hormones [21].

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4-Hydroxy-2-quinolones 7. Synthesis and biological properties of 1-R-3-(2-benzimidazolyl)-4-hydroxy-2-quinolones

Cited by 3 publications

References 0 publications

Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents

Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents

Design, Structure−Activity Relationships and in Vivo Characterization of 4-Amino-3-benzimidazol-2-ylhydroquinolin-2-ones: A Novel Class of Receptor Tyrosine Kinase Inhibitors

4-hydroxy-2-quinolones. 191.* synthesis, tautomerism and biological activity of benzimidazol-2-ylamides of 1-r-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids

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