The Chemistry of Isoquinolines.

Manske, Richard H. F.

doi:10.1021/cr60095a007

Cited by 31 publications

(5 citation statements)

References 58 publications

(66 reference statements)

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“…1) which lost the chiral group. Manske 23 had reported aluminum chloride as cyclizing agent for synthesis of tetrahydroisoquinolines at 1927. So aluminum chloride was used in our synthesis route as a mild catalyst and target compound 4 was obtained in a very satisfied yield (87.3 % yield).…”

Section: Resultsmentioning

confidence: 99%

An Efficient Synthesis of Dichotomine A via Cyclization of L-Tryptophan Derivative

Shi¹,

He²,

Li³

et al. 2013

Asian J. Chem.

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INTRODUCTION β-Carbolines represent a large group of alkaloids widely distributed in nature, occurring in plants, marine organisms and insects, most importantly, in foods and in human tissues and body fluids. They have diverse medicinal properties 1-6 such as inhibition of topoisomerase and monoamine oxidase, binding to benzodiazepine and serotonin receptors and intercalating into DNA. Dichotomines A, B, C and D, new β-carboline-type alkaloids, were first isolated from the roots of Stellaria dichotoma in 2004 7. They showed an antiallergic effect on ear passive cutaneous anaphylaxis reaction in mice and inhibitory activity on the release of β-hexosaminidase in RBL-2H3 cells. As shown in Fig. 1, the structure of dichotomines A, B, C and D include a chiral group respectively. Although many methodologies concerned the synthesis of β-carbolines 8-13 , the synthesis of dichotomines is quite limited. Dichotomine C was obtained by Omura and co-workers 14 based on the microwave assisted thermal electrocyclic reaction of a 1-azahexatriene system. Nemet and Defterdarovic 15 had synthesized dichotomine A as racemic mixture via reactions of L-tryptophan or L-tryptophan methyl ester with methyl glyoxal under acidic conditions. Zhang and co-works 16 had synthesized dichotomines A, B, C and D starting from L-tryptophan methyl ester and 2,3-Oisopropylidene-D-glyceraldehyde. From this total synthesis, dichotomine A was obtained in 13 steps and only in 24 % yield. So, we developed a new synthetic method for dichotomine A, which could reduce steps and obtain a higher yield. We chose L-tryptophan and L-lactic acid as raw material because they were inexpensive, commercially available and

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Section: Resultsmentioning

confidence: 99%

An Efficient Synthesis of Dichotomine A via Cyclization of L-Tryptophan Derivative

Shi¹,

He²,

Li³

et al. 2013

Asian J. Chem.

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“…The low yield in this cyclization reaction is primarily ascribed to the harsh reaction conditions and the difficulty in isolation of the products from the massive gummy reaction complex. Efforts to replace the toxic arsenic pentoxide by using other oxidants that were generally used in the Skraup reaction − (such as sodium 3-nitrobenzenesulfinate or green vitriol) were not successful. Instead, the double-cyclization product 5-(trifluoromethyl)-1,7-phenanthroline ( 16 ) was isolated as the major product.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and c-Met Kinase Inhibition of 3,5-Disubstituted and 3,5,7-Trisubstituted Quinolines: Identification of 3-(4-Acetylpiperazin-1-yl)-5-(3-nitrobenzylamino)-7- (trifluoromethyl)quinoline as a Novel Anticancer Agent

Wang

et al. 2011

J. Med. Chem.

104

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By use of an improved synthetic strategy, a series of 3,5-disubstituted and 3,5,7-trisubstituted quinolines were readily prepared. 3,5,7-Trisubstituted quinolines 21a-c, 21l, and 27a-c were identified as the most potent c-Met inhibitors with IC(50) of less than 1.0 nM. Compound 21b showed the most promising overall PK profile and has high potency and extraordinary selectivity to c-Met against c-Met family member Ron and 12 other tyrosine kinases. It produced constitutive inhibition of c-Met phosphorylation in c-Met dependent cell lines. At doses of 100 mg/kg, compound 21b showed statistically significant tumor growth inhibition (68-69%) in both NIH-3T3-TPR-Met and U-87 MG human gliobastoma xenograft models. These results clearly indicated that compound 21b is a potent and highly selective c-Met inhibitor. Its favorable in vitro and in vivo profiles warrant further investigation.

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“…The reaction appears to be of limited scope and gives low yields, and is only briefly mentioned in an older review of quinoline chemistry [276]. There is a modern development of the reaction in which AA is activated by thionyl chloride [277].…”

Section: Quinazolinesmentioning

confidence: 99%