Literature DB >> 18007389

Regioselective synthesis of novel N2- and N4-substituted 7-methylpyrazolo[4,5-e][1,2,4]thiadiazines.

Xinyong Liu1, Renzhang Yan, Niangen Chen, Wenfang Xu, Maria Teresa Molina, Salvador Vega.   

Abstract

The new compound 7-methylpyrazolo[4,5-e][1,2,4]thiadiazin-3(2H,4H)-one1,1-dioxide (5) was synthesized and its novel mono N2- or N4-substituted derivatives 6 and 7 were prepared by regioselective N-alkylation of 5 with different molar ratios of NaH and alkyl halides. Based on the regioselective alkylation conditions found a facile one-pot synthesis of N2,N4-disubstituted pyrazolo[4,5-e][1,2,4] thiadiazines 8 was developed. The structures of the newly synthesized compounds were confirmed by IR,(1)H-NMR, (13)C-NMR and MS spectral analysis.

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Year:  2006        PMID： 18007389      PMCID： PMC6148673          DOI： 10.3390/11110827

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


  9 in total

1.  Bioisosterism: A Rational Approach in Drug Design.

Authors:  George A. Patani; Edmond J. LaVoie
Journal:  Chem Rev       Date:  1996-12-19       Impact factor: 60.622

Review 2.  Potassium channel activator drugs: mechanism of action, pharmacological properties, and therapeutic potential.

Authors:  S D Longman; T C Hamilton
Journal:  Med Res Rev       Date:  1992-03       Impact factor: 12.944

Review 3.  Potassium channel modulators: scientific applications and therapeutic promise.

Authors:  D W Robertson; M I Steinberg
Journal:  J Med Chem       Date:  1990-06       Impact factor: 7.446

4.  3-(Alkylamino)-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxides as powerful inhibitors of insulin release from rat pancreatic B-cells: a new class of potassium channel openers?

Authors:  B Pirotte; P de Tullio; P Lebrun; M H Antoine; J Fontaine; B Masereel; M Schynts; L Dupont; A Herchuelz; J Delarge
Journal:  J Med Chem       Date:  1993-10-15       Impact factor: 7.446

5.  1,1,3-Trioxo-2H,4H-thieno[3,4-e][1,2,4]thiadiazine (TTD) derivatives: a new class of nonnucleoside human immunodeficiency virus type 1 (HIV-1) reverse transcriptase inhibitors with anti-HIV-1 activity.

Authors:  M Witvrouw; M E Arranz; C Pannecouque; R Declercq; H Jonckheere; J C Schmit; A M Vandamme; J A Diaz; S T Ingate; J Desmyter; R Esnouf; L Van Meervelt; S Vega; J Balzarini; E De Clercq
Journal:  Antimicrob Agents Chemother       Date:  1998-03       Impact factor: 5.191

6.  Imidazothiadiazine dioxides: synthesis and antiviral activity.

Authors:  A Martínez; A I Esteban; A Herrero; C Ochoa; G Andrei; R Snoeck; J Balzarini; E De Clercq
Journal:  Bioorg Med Chem       Date:  1999-08       Impact factor: 3.641

7.  Synthesis of some halogen-containing 1,2,4-triazolo-1,3,4-thiadiazines and their antibacterial and anticancer screening studies--part I.

Authors:  B S Holla; B K Sarojini; B S Rao; P M Akberali; N S Kumari; V Shetty
Journal:  Farmaco       Date:  2001-08

8.  4H-1,2,4-Pyridothiadiazine 1,1-dioxides and 2,3-dihydro-4H-1,2, 4-pyridothiadiazine 1,1-dioxides chemically related to diazoxide and cyclothiazide as powerful positive allosteric modulators of (R/S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors: design, synthesis, pharmacology, and structure-activity relationships.

Authors:  B Pirotte; T Podona; O Diouf; P de Tullio; P Lebrun; L Dupont; F Somers; J Delarge; P Morain; P Lestage; J Lepagnol; M Spedding
Journal:  J Med Chem       Date:  1998-07-30       Impact factor: 7.446

9.  Novel 1,1,3-trioxo-2H,4H-thieno[3,4-e][1,2,4]thiadiazine derivatives as non-nucleoside reverse transcriptase inhibitors that inhibit human immunodeficiency virus type 1 replication.

Authors:  E Arranz; J A Díaz; S T Ingate; M Witvrouw; C Pannecouque; J Balzarini; E De Clercq; S Vega
Journal:  J Med Chem       Date:  1998-10-08       Impact factor: 7.446
  9 in total

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