Literature DB >> 18007418

Lipid-lowering effects of ethyl 2-phenacyl-3-aryl-1H-pyrrole- 4-carboxylates in rodents.

Justin M Holub1, Kathy O'Toole-Colin, Adam Getzel, Anthony Argenti, Michael A Evans, Daniel C Smith, Gerard A Dalglish, Shahzad Rifat, Donna L Wilson, Brett M Taylor, Ulander Miott, Josephine Glersaye, Kam Suet Lam, Bryan J McCranor, Joshua D Berkowitz, Robert B Miller, John R Lukens, Keith Krumpe, John T Gupton, Bruce S Burnham.   

Abstract

A series of substituted 2-phenacyl-3-phenyl-1H-pyrrole-4-carboxylates were prepared from substituted acetophenones in 6 steps. The final condensations between a chloroenal and an aminoketone were carried out under neutral conditions in parallel to yield the series listed below. Selected pyrrole derivatives proved to be potent hypolipidemic agents lowering serum triglyceride concentrations in CF-1 male mice after 14 days of I.P. administration. One agent orally lowered serum cholesterol in Sprague-Dawley male rats at 2mg/kg/day after 14 days. The agents demonstrated a lowering of mouse serum LDL- cholesterol levels and selected compounds showed an elevation of serum HDL-cholesterol levels. The cholesterol concentrations in the liver were raised while the cholesterol and triglyceride contents of the aorta were significantly lowered by the selected trisubstituted pyrrole.

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Year:  2004        PMID: 18007418      PMCID: PMC6147299          DOI: 10.3390/90300134

Source DB:  PubMed          Journal:  Molecules        ISSN: 1420-3049            Impact factor:   4.411


  31 in total

1.  Cytotoxicity of substituted alkyl-3,4-bis(4-methoxyphenyl)pyrrole-2-carboxylates in L1210 lymphoid leukemia cells.

Authors:  B S Burnham; J T Gupton; K Krumpe; T Webb; J Shuford; B Bowers; A E Warren; C Barnes; I H Hall
Journal:  Arch Pharm (Weinheim)       Date:  1998-11       Impact factor: 3.751

2.  Reduction in levels of 24S-hydroxycholesterol by statin treatment in patients with Alzheimer disease.

Authors:  Gloria Lena Vega; Myron F Weiner; Anne M Lipton; Klaus Von Bergmann; Dieter Lutjohann; Carol Moore; Doris Svetlik
Journal:  Arch Neurol       Date:  2003-04

3.  Synthesis and biological activity of methanesulfonamide pyrimidine- and N-methanesulfonyl pyrrole-substituted 3,5-dihydroxy-6-heptenoates, a novel series of HMG-CoA reductase inhibitors.

Authors:  M Watanabe; H Koike; T Ishiba; T Okada; S Seo; K Hirai
Journal:  Bioorg Med Chem       Date:  1997-02       Impact factor: 3.641

4.  Synthesis and cytotoxicity of 2,4-disubstituted and 2,3,4-trisubstituted brominated pyrroles in murine and human cultured tumor cells.

Authors:  J T Gupton; B S Burham; K Krumpe; K Du; J A Sikorski; A E Warren; C R Barnes; I H Hall
Journal:  Arch Pharm (Weinheim)       Date:  2000-01       Impact factor: 3.751

Review 5.  Relation between cholesterol levels, statins and Alzheimer's disease in the human population.

Authors:  B Austen; G Christodoulou; J E Terry
Journal:  J Nutr Health Aging       Date:  2002       Impact factor: 4.075

6.  The cytotoxicity and mode of action of 2,3,4-trisubstituted pyrroles and related derivatives in human Tmolt4 leukemia cells.

Authors:  J T Gupton; B S Burham; B D Byrd; K E Krumpe; C Stokes; J Shuford; S Winkle; T Webb; A E Warren; C R Barnes; J Henry; I H Hall
Journal:  Pharmazie       Date:  1999-09       Impact factor: 1.267

7.  A novel anti-inflammatory role for simvastatin in inflammatory arthritis.

Authors:  Bernard P Leung; Naveed Sattar; Anne Crilly; Morag Prach; David W McCarey; Helen Payne; Rajan Madhok; Carol Campbell; J Alastair Gracie; Foo Y Liew; Iain B McInnes
Journal:  J Immunol       Date:  2003-02-01       Impact factor: 5.422

8.  Antihyperlipidemic activity of sesquiterpene lactones and related compounds.

Authors:  I H Hall; K H Lee; C O Starnes; O Muraoka; Y Sumida; T G Waddell
Journal:  J Pharm Sci       Date:  1980-06       Impact factor: 3.534

9.  Inhibitors of cholesterol biosynthesis. 2. 3,5-Dihydroxy-7-(N-pyrrolyl)-6-heptenoates, a novel series of HMG-CoA reductase inhibitors.

Authors:  P A Procopiou; C D Draper; J L Hutson; G G Inglis; B C Ross; N S Watson
Journal:  J Med Chem       Date:  1993-11-12       Impact factor: 7.446

10.  Hypolipidemic activity of amine-borane aducts of cyclohexylamine and toluidine in rodents.

Authors:  B S Burnham; S Y Chen; A Sood; B F Spielvogel; I H Hall
Journal:  Met Based Drugs       Date:  1995
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  6 in total

1.  Novel 5-substituted benzyloxy-2-arylbenzofuran-3-carboxylic acids as calcium activated chloride channel inhibitors.

Authors:  Satish Kumar; Wan Namkung; A S Verkman; Pawan K Sharma
Journal:  Bioorg Med Chem       Date:  2012-06-06       Impact factor: 3.641

2.  Amaranzoles B-F, imidazole-2-carboxy steroids from the marine sponge Phorbas amaranthus. C24-N- and C24-O-analogues from a divergent oxidative biosynthesis.

Authors:  Brandon I Morinaka; Joseph R Pawlik; Tadeusz F Molinski
Journal:  J Org Chem       Date:  2010-04-16       Impact factor: 4.354

Review 3.  Lamellarins and related pyrrole-derived alkaloids from marine organisms.

Authors:  Hui Fan; Jiangnan Peng; Mark T Hamann; Jin-Feng Hu
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

4.  Characterization of novel diaryl oxazole-based compounds as potential agents to treat pancreatic cancer.

Authors:  Arthur Y Shaw; Meredith C Henderson; Gary Flynn; Betty Samulitis; Haiyong Han; Steve P Stratton; H-H Sherry Chow; Laurence H Hurley; Robert T Dorr
Journal:  J Pharmacol Exp Ther       Date:  2009-08-05       Impact factor: 4.030

5.  A simple approach to the synthesis of highly functionalized 3-alkylidene-2,3-dihydro-1H-pyrrole-2-ol derivatives and related pyrroles.

Authors:  Farough Nasiri; Kourosh Pourdavaie
Journal:  Mol Divers       Date:  2007-04-04       Impact factor: 3.364

6.  Crystal structures of methyl 3-(4-iso-propyl-phen-yl)-1-methyl-1,2,3,3a,4,9b-hexa-hydro-thio-chromeno[4,3-b]pyrrole-3a-carboxyl-ate, methyl 1-methyl-3-(o-tol-yl)-1,2,3,3a,4,9b-hexa-hydro-thio-chromeno[4,3-b]pyrrole-3a-carboxyl-ate and methyl 1-methyl-3-(o-tol-yl)-3,3a,4,9b-tetra-hydro-1H-thio-chromeno[4,3-c]isoxazole-3a-carboxyl-ate.

Authors:  R Raja; M Suresh; R Raghunathan; A SubbiahPandi
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-05-07
  6 in total

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