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Design and synthesis of hepatoselective, pyrrole-based HMG-CoA reductase inhibitors.

Pfefferkorn JA, Song Y, Sun KL, Miller SR, Trivedi BK, Choi C, Sorenson RJ, Bratton LD, Unangst PC, Larsen SD, Poel TJ, Cheng XM, Lee C, Erasga N, Auerbach B, Askew V, Dillon L, Hanselman JC, Lin Z, Lu G, Robertson A, Olsen K, Mertz T, Sekerke C, Pavlovsky A, Harris MS, Bainbridge G, Caspers N, Chen H, Eberstadt M
Bioorg Med Chem Lett 17 4538-44 (2007)
Cited: 30 times
EuropePMC logo PMID: 17574412

Abstract

This manuscript describes the design and synthesis of a series of pyrrole-based inhibitors of HMG-CoA reductase for the treatment of hypercholesterolemia. Analogs were optimized using structure-based design and physical property considerations resulting in the identification of 44, a hepatoselective HMG-CoA reductase inhibitor with excellent acute and chronic efficacy in a pre-clinical animal models.

Reviews - 2q1l mentioned but not cited (1)

  1. An Atomic-Level Perspective of HMG-CoA-Reductase: The Target Enzyme to Treat Hypercholesterolemia. Gesto DS, Pereira CMS, Cerqueira NMFS, Sousa SF. Molecules 25 (2020)

Articles - 2q1l mentioned but not cited (11)

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  2. Drug screening on Hutchinson Gilford progeria pluripotent stem cells reveals aminopyrimidines as new modulators of farnesylation. Blondel S, Egesipe AL, Picardi P, Jaskowiak AL, Notarnicola M, Ragot J, Tournois J, Le Corf A, Brinon B, Poydenot P, Georges P, Navarro C, Pitrez PR, Ferreira L, Bollot G, Bauvais C, Laustriat D, Mejat A, De Sandre-Giovannoli A, Levy N, Bifulco M, Peschanski M, Nissan X. Cell Death Dis 7 e2105 (2016)
  3. CrossDocker: a tool for performing cross-docking using Autodock Vina. Shamsara J. Springerplus 5 344 (2016)
  4. An Insight Into Structure, Function, and Expression Analysis of 3-Hydroxy-3-Methylglutaryl-CoA Reductase of Cymbopogon winterianus. Devi K, Patar L, Modi MK, Sen P. Bioinform Biol Insights 11 1177932217701735 (2017)
  5. Lovastatin lactone may improve irritable bowel syndrome with constipation (IBS-C) by inhibiting enzymes in the archaeal methanogenesis pathway. Muskal SM, Sliman J, Kokai-Kun J, Pimentel M, Wacher V, Gottlieb K. F1000Res 5 606 (2016)
  6. Plausible computational insights and new atomic-level perspective of epicathechin gallate from Crataegus oxycantha extract in preventing caspase 3 activation in conditions like post-myocardial infarction. Ravindran ASK, Venkatabalasubramanian S, Manickam R, Anusuyadevi M, K Swaminathan J. J Biomol Struct Dyn 40 3400-3415 (2022)
  7. The Development of Target-Specific Pose Filter Ensembles To Boost Ligand Enrichment for Structure-Based Virtual Screening. Xia J, Hsieh JH, Hu H, Wu S, Wang XS. J Chem Inf Model 57 1414-1425 (2017)
  8. 7-Acetoxyhorminone from Salvia multicaulis Vahl. as Promising Inhibitor of 3-Hydroxy-3-methylglutaryl Coenzyme A (HMG-CoA) Reductase. Yigitkan S, Ertas A, Salmas RE, Firat M, Orhan IE. Pharmaceuticals (Basel) 15 198 (2022)
  9. In silico investigation on alkaloids of Rauwolfia serpentina as potential inhibitors of 3-hydroxy-3-methyl-glutaryl-CoA reductase. Azmi MB, Sultana S, Naeem S, Qureshi SA. Saudi J Biol Sci 28 731-737 (2021)
  10. In Silico Characterization of Withania coagulans Bioactive Compounds as Potential Inhibitors of Hydroxymethylglutaryl (HMG-CoA) Reductase of Mus musculus. Azmi MB, Khan F, Asif U, Khurshid B, Wadood A, Qureshi SA, Ahmed SDH, Mudassir HA, Sheikh SI, Feroz N. ACS Omega 8 5057-5071 (2023)
  11. Selected Soybean Varieties Regulate Hepatic LDL-Cholesterol Homeostasis Depending on Their Glycinin:β-Conglycinin Ratio. Rebollo-Hernanz M, Bringe NA, Gonzalez de Mejia E. Antioxidants (Basel) 12 20 (2022)


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  1. The role of statins in both cognitive impairment and protection against dementia: a tale of two mechanisms. Schultz BG, Patten DK, Berlau DJ. Transl Neurodegener 7 5 (2018)
  2. Statins therapy: a review on conventional and novel formulation approaches. Tiwari R, Pathak K. J Pharm Pharmacol 63 983-998 (2011)
  3. Novel 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors: a patent review. Pfefferkorn JA. Expert Opin Ther Pat 21 187-203 (2011)
  4. Utility of early high dose statins in acute coronary syndrome. Dougherty PJ, Arora RR. Am J Ther 19 369-376 (2012)

Articles citing this publication (14)

  1. Lipophilic but not hydrophilic statins selectively induce cell death in gynaecological cancers expressing high levels of HMGCoA reductase. Kato S, Smalley S, Sadarangani A, Chen-Lin K, Oliva B, Brañes J, Carvajal J, Gejman R, Owen GI, Cuello M. J Cell Mol Med 14 1180-1193 (2010)
  2. Statin therapy and association with ovarian cancer risk in the New England Case Control (NEC) study. Akinwunmi B, Vitonis AF, Titus L, Terry KL, Cramer DW. Int J Cancer 144 991-1000 (2019)
  3. Association of Cognitive Impairment in Patients on 3-Hydroxy-3-Methyl-Glutaryl-CoA Reductase Inhibitors. Roy S, Weinstock JL, Ishino AS, Benites JF, Pop SR, Perez CD, Gumbs EA, Rosenbaum JA, Roccato MK, Shah H, Contino G, Hunter K. J Clin Med Res 9 638-649 (2017)
  4. Effect of atorvastatin on pancreatic Beta-cell function and insulin resistance in type 2 diabetes mellitus patients: a randomized pilot study. Goyal A, Singh S, Tandon N, Gupta N, Gupta YK. Can J Diabetes 38 466-472 (2014)
  5. Pharmacophore generation and atom-based 3D-QSAR of N-iso-propyl pyrrole-based derivatives as HMG-CoA reductase inhibitors. Teli MK, K RG. Org Med Chem Lett 2 25 (2012)
  6. Exploration of virtual candidates for human HMG-CoA reductase inhibitors using pharmacophore modeling and molecular dynamics simulations. Son M, Baek A, Sakkiah S, Park C, John S, Lee KW. PLoS One 8 e83496 (2013)
  7. Molecular modeling studies of atorvastatin analogues as HMGR inhibitors using 3D-QSAR, molecular docking and molecular dynamics simulations. Wang Z, Cheng L, Kai Z, Wu F, Liu Z, Cai M. Bioorg Med Chem Lett 24 3869-3876 (2014)
  8. DOX: A new computational protocol for accurate prediction of the protein-ligand binding structures. Rao L, Chi B, Ren Y, Li Y, Xu X, Wan J. J Comput Chem 37 336-344 (2016)
  9. A copper-catalyzed coupling reaction of vinyl halides and carbazates: application in the assembly of polysubstituted pyrroles. Zhou C, Ma D. Chem Commun (Camb) 50 3085-3088 (2014)
  10. Monoamine oxidase inhibitors: benzylidene-prop-2-ynyl-amines analogues. Jia Z, Wei S, Zhu Q. Biol Pharm Bull 33 725-728 (2010)
  11. Statin activation of skeletal ryanodine receptors (RyR1) is a class effect but separable from HMG-CoA reductase inhibition. Lindsay C, Musgaard M, Russell AJ, Sitsapesan R. Br J Pharmacol 179 4941-4957 (2022)
  12. A fungal tolerance trait and selective inhibitors proffer HMG-CoA reductase as a herbicide mode-of-action. Haywood J, Breese KJ, Zhang J, Waters MT, Bond CS, Stubbs KA, Mylne JS. Nat Commun 13 5563 (2022)
  13. Cognitive Function Assessment in Patients on Moderate- or High-Intensity Statin Therapy. Roy S, Hyman D, Ayyala S, Bakhshi A, Kim SH, Anoruo N, Weinstock J, Balogun A, D'Souza M, Filatova N, Penabad J, Shah P, Perez C, Mehta A, Hunter K. J Clin Med Res 12 255-265 (2020)
  14. The Role of Lipid Rafts and Membrane Androgen Receptors in Androgen's Neurotoxic Effects. Fadeyibi O, Rybalchenko N, Mabry S, Nguyen DH, Cunningham RL. J Endocr Soc 6 bvac030 (2022)


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