Substituted dihydrobenzopyran and dihydrobenzofuran thiazolidine-2,4-diones as hypoglycemic agents

Clark, David A.; Goldstein, Solomon; Volkmann, Robert A.; Eggler, James F.; Holland, Gerald F.; Hulin, Bernard; Stevenson, R. W.; Kreutter, David K.; Gibbs, E. Michael

doi:10.1021/jm00105a050

Cited by 67 publications

(31 citation statements)

References 2 publications

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“…metformin) [90]. Recently, a new class of antidiabetic agents, the thiazolidinediones, has been developed and clinically evaluated [91, 92]. As a class, thiazolidinediones have been shown to enhance peripheral insulin sensitivity in animal models of insulin resistance [93, 94]and type II diabetic patients [95].…”

Section: Can Diabetes Be Treated?mentioning

confidence: 99%

Atypical Antipsychotic Drug Use and Diabetes

Ananth

Venkatesh

Burgoyne

et al. 2002

Psychother Psychosom

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Recently, there has been increased concern about the occurrence of diabetes associated with the use of atypical antipsychotic (AAP) drugs. The relationship between diabetes, schizophrenia, and antipsychotic drugs is complex and intriguing, as untreated patients with schizophrenia are known to suffer from diabetes more often than the general population. Thirty individual case reports of clozapine-, 26 cases of olanzapine- and a few others of seroquel- and risperidone-associated diabetes mellitus, hyperglycemia and diabetic ketoacidosis were found by a Medline search. The case reports do not provide the incidence of diabetes in patients treated with AAP drugs, but they suggest that AAP drugs may cause hyperglycemia. Further research is needed to identify the cause of the susceptibility of the schizophrenic population, and to elucidate the mechanisms by which the antipsychotic drugs either cause diabetes or precipitate its onset. Which antipsychotic drugs have a higher and which have a lower potential to induce diabetes is not conclusively answered at present. However, the findings that 50% of the patients completely improve upon drug discontinuation, and that hyperglycemia promptly recurs upon reinstitution of the incriminated drug indicate that this side effect is reversible and is drug related. African Americans are particularly susceptible to AAP drug-induced diabetes. Until the new research data become available, AAP drug treatment of schizophrenic patients aims at prevention, institution of vigilant screening procedures, and management of hyperglycemia.

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Section: Can Diabetes Be Treated?mentioning

confidence: 99%

Atypical Antipsychotic Drug Use and Diabetes

Ananth

Venkatesh

Burgoyne

et al. 2002

Psychother Psychosom

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“…Further, in vivo oral hypoglycemic activity of selected compounds of this series were further evaluated in genetically obese ob/ob mouse. On the basis of in vivo potency as well as additional profiling in alternative animal models, to resolved dihydrobenzopyran containing englitazone (8) was selected for clinical trial study 31 shows more potent activity in adipocytes differentiation assay and good hypoglycemic activity. In addition, hydrochloric salt of (11) was prepared and selected as a testing candidate over rosiglitazone (4) for a clinical study.…”

Section: 30mentioning

confidence: 99%

“…▪ Inclusion of central phenoxyalkyl linker (B) into a different heterocyclic rings are also leads to active thiazolidine-2,4-diones, which are including englitazone (8) 31 , T-174 (22) 52 and edaglitazone (25) 56 . ▪ Replacement of central phenoxyalkyl linker (B) by naphthalene ring to give netoglitazone (14) compound of thiazolidine-2,4-diones class, which show more potent activity, as compared to rosiglitazone (4) 44 .…”

mentioning

confidence: 99%

Thiazolidine-2,4-Diones: An Update Review of Antidiabetic Agents

Dumbare¹,

Kawale²,

Nade³

et al. 2018

Int. Res. J. Pharm.

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Diabetes mellitus is a serious global health problem and taking its place as one of the main threats to human health in the 21 st century. The National Diabetes Information Clearinghouse & World Health Organization shows above 90% of the diabetic population fall under type 2 diabetes mellitus category. The treatment generally prescribed for type 2 diabetes mellitus has been a combination of diet, exercise and current therapeutic agents Due to their adverse effects and side effects, most of these treatments are considered to be unsatisfactory in terms of preventio n of complications and preservation of quality of life. The current therapeutic agents containing thiazolidine-2,4-diones or glitazones are shown better treatment on type 2 diabetes mellitus via acting on peroxisome proliferator-activated receptor-gamma (PPAR-γ). From these glitazones, troglitazone and rosiglitazone are withdrawn from markets. Pioglitazone and lobeglitazone are used in market. Ciglitazone, englitazone, darglitazone, KRP-297, rivoglitazone and CLX-921 are discontinued in various clinical trials. Mitoglitazone, netoglitazone and balaglitazone are present in various phases of clinical trials. Furthermore, based on various literature surveys, we are studied in details structure activity relationships of various glitazones.

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“…[49][50][51][52][53][54][55] In 2002, Grigg and co-workers reported an interesting Pd-catalyzed queuing processes by employing allene as a relay switch and secondary amines as nucleophiles. 39 Inspired by these precedents and our continued interest in the palladium-catalyzed cross-coupling of N-tosylhydrazones, [56][57][58][59] we conceived that the alkyl-Pd species generated from intramolecular carbopalladation of alkene may be trapped by a diazo substrate to form a Pd carbene species, which would undergo migratory insertion and β-hydride elimination to afford the polysubstituted olefins (Scheme 1c).…”

Section: Introductionmentioning

confidence: 99%

Pd-Catalyzed Highly Regio- and Stereoselective Formation of C–C Double Bonds: An Efficient Method for the Synthesis of Benzofuran-, Dihydrobenzofuran-, and Indoline-Containing Alkenes

et al. 2015

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A highly regio- and stereoselective C-C double bond formation reaction via Pd-catalyzed Heck-type cascade process with N-tosylhydrazones has been developed. Various N-tosylhydrazones derived from both ketones and aldehydes are found to be efficient substrates to provide di- and trisubstituted olefins with high regio- and stereoselectivity. Furthermore, this reaction has a good functional group tolerance and different benzofuran-, dihydrobenzofuran-, and indoline-containing alkene products were obtained with high selectivity.

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Substituted dihydrobenzopyran and dihydrobenzofuran thiazolidine-2,4-diones as hypoglycemic agents

Cited by 67 publications

References 2 publications

Atypical Antipsychotic Drug Use and Diabetes

Atypical Antipsychotic Drug Use and Diabetes

Thiazolidine-2,4-Diones: An Update Review of Antidiabetic Agents

Pd-Catalyzed Highly Regio- and Stereoselective Formation of C–C Double Bonds: An Efficient Method for the Synthesis of Benzofuran-, Dihydrobenzofuran-, and Indoline-Containing Alkenes

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