期刊文献+

One-pot Synthesis,Crystal Structures and Antimicrobial Activities of Two New 1,4-Disubstituted 1,2,3-Triazole-4-Carboxylates 被引量:2

One-pot Synthesis,Crystal Structures and Antimicrobial Activities of Two New 1,4-Disubstituted 1,2,3-Triazole-4-Carboxylates
下载PDF
导出
摘要 Two new 1,4-disubstituted 1,2,3-triazoles-4-carboxylates were synthesized via click reaction. Compound 1a was synthesized by the interaction of 6-nitro-tetrazolo[1.5-a]-pyridine with ethyl propynoate at room temperature in the presence of Cu(OAc)2 as a catalyst and THF as solvent. Compound 1b was also synthesized by the same manner except that tert-butyl propionate, instead of ethyl propynoate, was used. The compounds were characterized by IR, 1H-NMR, 13C-NMR and single-crystal X-ray diffraction analysis. Compound 1a(C10H9N5O4) crystallizes in the triclinic system, space group P1 with a = 5.0894(9), b = 8.9834(13), c = 13.089(2) ?, α= 83.041(7), β= 80.256(7), γ=87.296(8)°, V = 585.24(16)?3, Z = 2, Mr = 263.22, crystal size(mm) = 0.37 × 0.20 ×0.18,(I 〉 2σ(I)) = 8557, 2493, 1229, Rint = 0.057. Compound 1b(C12H13N5O4) crystallizes in the monoclinic system, space group P21/c with a = 6.8854(5), b = 21.783(2), c = 9.3986(8) ?,β = 93.239(4)°, V = 1407.4(2)?3, Z = 4, Mr = 291.27, crystal size(mm) = 0.38 × 0.22 × 0.20,(I 〉 2σ(I)) = 11842, 3172, 1866, Rint = 0.047. Antimicrobial assay results showed that the title compounds display excellent activities to different bacterial and fungal strains. Two new 1,4-disubstituted 1,2,3-triazoles-4-carboxylates were synthesized via click reaction. Compound 1a was synthesized by the interaction of 6-nitro-tetrazolo[1.5-a]-pyridine with ethyl propynoate at room temperature in the presence of Cu(OAc)2 as a catalyst and THF as solvent. Compound 1b was also synthesized by the same manner except that tert-butyl propionate, instead of ethyl propynoate, was used. The compounds were characterized by IR, 1H-NMR, 13C-NMR and single-crystal X-ray diffraction analysis. Compound 1a(C10H9N5O4) crystallizes in the triclinic system, space group P1 with a = 5.0894(9), b = 8.9834(13), c = 13.089(2) ?, α= 83.041(7), β= 80.256(7), γ=87.296(8)°, V = 585.24(16)?3, Z = 2, Mr = 263.22, crystal size(mm) = 0.37 × 0.20 ×0.18,(I 〉 2σ(I)) = 8557, 2493, 1229, Rint = 0.057. Compound 1b(C12H13N5O4) crystallizes in the monoclinic system, space group P21/c with a = 6.8854(5), b = 21.783(2), c = 9.3986(8) ?,β = 93.239(4)°, V = 1407.4(2)?3, Z = 4, Mr = 291.27, crystal size(mm) = 0.38 × 0.22 × 0.20,(I 〉 2σ(I)) = 11842, 3172, 1866, Rint = 0.047. Antimicrobial assay results showed that the title compounds display excellent activities to different bacterial and fungal strains.
出处 《Chinese Journal of Structural Chemistry》 SCIE CAS CSCD 2015年第1期26-32,共7页 结构化学(英文)
基金 supported by the Higher Education Commision(HEC),Govt.of Pakistan
关键词 click reaction TRIAZOLES crystal structure antimicrobial activity click reaction, triazoles, crystal structure, antimicrobial activity
  • 相关文献

参考文献20

  • 1Purcell, W. P.; Singer, J. A. Electronic and molecular structure of selected unsubstituted and dimethyl amides from measurements of electric moments and nuclear magnetic resonance. J. Phys. Chem. 1967, 71, 4316-4319.
  • 2Chemama, M.; Fonvielle, M.; Arthur, M.; Valety, J. M.; Etheve-Quelquejeu, M. Synthesis of stable aminoacyl-tRNA analogues containing triazole as a bioisoster of esters. Chem.-A Eur. 3'. 2009, 15, ]929-1938.
  • 3Fray, M. J.; Bull, D. J.; Can, C. L.; Gautier, E. C.; Mowbray, C. E.; Stobie, A. Structure-activity relationships of 1,4-dihydro-(l H, 4H)-quinoxaline- 2, 3-diones as N-methyI-D-aspartate (glycine site) receptor antagonists. I. lleterocyclic substituted 5-alkyl derivatives~ J. Med. Chem. 2001, 44, 1951-1962.
  • 4Smith, G.; Glaser, M.; Perumal, M.; Nguyen, Q. D.; Shan, B.; ./trstad, E.; Aboagye, E. O. Design, synthesis and biological characterization of a caspase 3/7 selective isatin labeled with 2-[18F] fluoroethylazide. 3. Med. Chem. 2008, 51, 8057-8067.
  • 5Yim, C. B.; Dijkgraaf, I.; Merkx, R.; Versluis, C.; Eek, A.; Mulder, G. E.; Rijkers, D. T.; Boetman, O. C.; Liskamp, R. M. Synthesis of DOTA- conjugated multimeric [Tyr3] octreotide peptides via a combination of Cu(l)-catalyzed "click" cycloaddition and thio acid/sullbnyl azide "sulfo- click" amidation and their in vivo evaluation, d. Med. Chem. 2010, 53, 3944-3953.
  • 6Vatmurge, N. S.; Hazra, B. G.; Pore, V. S.; Shirazi, F.; Chavan, P. S.; Deshpande, M. V. Synthesis and antimicrobial activity offl-lactam-bile acid conjugates linked via triazole. Bioorg. Med. Chem, Lett. 2008, 18, 2043-2047.
  • 7Vatmurge N. S.; Hazra, B. G.; Pore, V. S.; Shirazi, F.; Deshpande, M. V.; Kadreppa, $4 Chattopadhyay, S.; Gonnade, R, G. Synthesis and biological evaluation of bile acid dimers linked with 1,2,3-triazole and bis-fl-lactam. Org. Biomol. Chem. 2008, 6, 3823-3830.
  • 8Somu, R. V.; Boshoff, H.; Qiao, C.; Bennett, E. M.; Barry, C. E.; Aldrich, C. C. Rationally designed nucleoside antibiotics that inhibit siderophore biosynthesis of mycobacterium tuberculosis. J. Med. Chem. 2006, 49, 31-34.
  • 9Costa, M. S.; Boechat, N.; Rangel, 1~. A.; Da Silva, F. D. C.; De Souza, A. M.; Rodrigues, C. R.; Castro, H C; Junior, 1. N.; Louren~o, M. C. S.; Wardell, S. M. Synthesis, tuberculosis inhibitory activity, and SAR study of N-substituted-phenyl-1, 2, 3-triazole derivatives. Bioorg. Ailed Chem. 2006, 14, 8644-8653.
  • 10Whiting, M.; Tripp, J. C.; Lin, Y. C.; Lindstrom, W.; Olson, A. J.; Elder, J. H.; Sharpless, K. B.; Fokin, V. V. Rapid discovery and structure-activity profiling of novel inhibitors of human immunodeficiency virus type 1 protease enabled by the copper(l)-catalyzed synthesis of 1,2,3-triazoles and their further functionalization. J. Med. Chem. 2006, 49, 7697-7710.

同被引文献2

引证文献2

二级引证文献1

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部