Literature DB >> 24273442

An efficacious protocol for C-4 substituted 3,4-dihydropyrimidinones. Synthesis and calcium channel binding studies.

Kamaljit Singh1, Divya Arora, Danielle Falkowski, Qingxin Liu, Robert S Moreland.   

Abstract

Ethyl 1,2-dihydro-1,6-dimethyl/6-methyl-2-oxopyrimidine-5-carboxylates react with C-nucleophiles as well as anion of enantiopure chiral auxiliary (1Rn class="Chemical">,2S,5R)-(-)-methyl (S)-p-toluenesulfinate to afford C-4 substituted and enantiopure congeners of medicinally potent Biginelli dihydropyrimidinones. The calcium channel blocking activity of some of the compounds was evaluated and compared with nifedipine for their ability to relax a membrane depolarization induced contraction.

Entities:  

Keywords:  Biginelli reaction; chiral sulfoxide; lithiation; regioselective addition; vascular smooth muscles

Year:  2009        PMID： 24273442      PMCID： PMC3834990          DOI： 10.1002/ejoc.200900208

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  27 in total

1.  Dissecting cellular processes using small molecules: identification of colchicine-like, taxol-like and other small molecules that perturb mitosis.

Authors:  S J Haggarty; T U Mayer; D T Miyamoto; R Fathi; R W King; T J Mitchison; S L Schreiber
Journal:  Chem Biol       Date:  2000-04

2.  Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen.

Authors:  T U Mayer; T M Kapoor; S J Haggarty; R W King; S L Schreiber; T J Mitchison
Journal:  Science       Date:  1999-10-29       Impact factor: 47.728

Review 3.  Genesis of dihydropyrimidinone(psi) calcium channel blockers: recent progress in structure-activity relationships and other effects.

Authors:  K Singh; D Arora; K Singh; S Singh
Journal:  Mini Rev Med Chem       Date:  2009-01       Impact factor: 3.862

4.  Metalation of Biginelli compounds. A general unprecedented route to C-6 functionalized 4-aryl-3,4-dihydropyrimidinones.

Authors:  Kamaljit Singh; Sukhdeep Singh; Aman Mahajan
Journal:  J Org Chem       Date:  2005-07-22       Impact factor: 4.354

5.  Calcium entry blockers and activators: conformational and structural determinants of dihydropyrimidine calcium channel modulators.

Authors:  G C Rovnyak; S D Kimball; B Beyer; G Cucinotta; J D DiMarco; J Gougoutas; A Hedberg; M Malley; J P McCarthy; R Zhang
Journal:  J Med Chem       Date:  1995-01-06       Impact factor: 7.446

6.  In vitro and in vivo evaluation of dihydropyrimidinone C-5 amides as potent and selective alpha(1A) receptor antagonists for the treatment of benign prostatic hyperplasia.

Authors:  J C Barrow; P G Nantermet; H G Selnick; K L Glass; K E Rittle; K F Gilbert; T G Steele; C F Homnick; R M Freidinger; R W Ransom; P Kling; D Reiss; T P Broten; T W Schorn; R S Chang; S S O'Malley; T V Olah; J D Ellis; A Barrish; K Kassahun; P Leppert; D Nagarathnam; C Forray
Journal:  J Med Chem       Date:  2000-07-13       Impact factor: 7.446

7.  Highly enantioselective organocatalytic Biginelli reaction.

Authors:  Xiao-Hua Chen; Xiao-Ying Xu; Hua Liu; Lin-Feng Cun; Liu-Zhu Gong
Journal:  J Am Chem Soc       Date:  2006-11-22       Impact factor: 15.419

8.  An enantioselective biginelli reaction catalyzed by a simple chiral secondary amine and achiral brønsted acid by a dual-activation route.

Authors:  Junguo Xin; Lu Chang; Zongrui Hou; Deju Shang; Xiaohua Liu; Xiaoming Feng
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

9.  Characterization of a thermally induced irreversible conformational transition of amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase in enantioseparation of dihydropyrimidinone acid by quasi-equilibrated liquid chromatography and solid-state NMR.

Authors:  Fang Wang; Robert M Wenslow; Thomas M Dowling; Karl T Mueller; Ivan Santos; Jean M Wyvratt
Journal:  Anal Chem       Date:  2003-11-01       Impact factor: 6.986

10.  N1-Alkylated 3,4-dihydropyrimidine-2(1H)-ones: Convenient one-pot selective synthesis and evaluation of their calcium channel blocking activity.

Authors:  Kamaljit Singh; Divya Arora; Elizabeth Poremsky; Jazmyne Lowery; Robert S Moreland
Journal:  Eur J Med Chem       Date:  2008-10-11       Impact factor: 6.514
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  3 in total

1.  Discovery of 3,4-Dihydropyrimidin-2(1H)-ones As a Novel Class of Potent and Selective A2B Adenosine Receptor Antagonists.

Authors:  Abel Crespo; Abdelaziz El Maatougui; Pierfrancesco Biagini; Jhonny Azuaje; Alberto Coelho; José Brea; María Isabel Loza; María Isabel Cadavid; Xerardo García-Mera; Hugo Gutiérrez-de-Terán; Eddy Sotelo
Journal:  ACS Med Chem Lett       Date:  2013-10-03       Impact factor: 4.345

2.  An efficient synthesis of enantiopure (R)-heteroarylpyrimidine analogs.

Authors:  Xiu-Yan Yang; Guang-Qiang Xia; Xiao-Kui Wang; Zhi-Bing Zheng; Dong-Mei Zhao; Guo-Ming Zhao; Song Li
Journal:  Molecules       Date:  2013-09-11       Impact factor: 4.411

Review 3.  Synthesis of 3,4-Dihydropyrimidin(thio)one Containing Scaffold: Biginelli-like Reactions.

Authors:  Francisco Sánchez-Sancho; Marcos Escolano; Daniel Gaviña; Aurelio G Csáky; María Sánchez-Roselló; Santiago Díaz-Oltra; Carlos Del Pozo
Journal:  Pharmaceuticals (Basel)       Date:  2022-07-30
  3 in total

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