메뉴 건너뛰기




Volumn 16, Issue 5, 2013, Pages 400-407

Microwave-assisted combinatorial synthesis of 2-Alkyl-2- (narylsulfonylindol- 3-yl)-3-N-Acyl-5-Aryl-1,3,4-oxadiazolines as anti-HIV- 1 agents

Author keywords

1,3,4 oxadiazoline; Human immunodeficiency virus 1; Inhibitor; Microwave heating

Indexed keywords

2 ALKYL 2 (N ARYLSULFONYLINDOL 3 YL) 3 N ACYL 5 ARYL 1,3,4 OXADIAZOLINE; ACID ANHYDRIDE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; HYDRAZONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84877958805     PISSN: 13862073     EISSN: 18755402     Source Type: Journal    
DOI: 10.2174/1386207311316050005     Document Type: Article
Times cited : (7)

References (30)
  • 1
    • 68449083305 scopus 로고    scopus 로고
    • Developments of indoles as anti-HIV-1 inhibitors
    • Xu, H.; Lv, M. Developments of indoles as anti-HIV-1 inhibitors. Curr. Pharm. Des., 2009, 15, 2120-2148.
    • (2009) Curr. Pharm. Des. , vol.15 , pp. 2120-2148
    • Xu, H.1    Lv, M.2
  • 2
    • 0037130296 scopus 로고    scopus 로고
    • New developments in anti-HIV chemotherapy
    • De Clercq, E. New developments in anti-HIV chemotherapy. Biochim. Biophys. Acta, 2002, 1587, 258-275.
    • (2002) Biochim. Biophys. Acta , vol.1587 , pp. 258-275
    • De Clercq, E.1
  • 3
    • 0027179491 scopus 로고
    • Preent status and future prospects for HIV therapies
    • Johnston, M.I.; Hoth, D.F. Preent status and future prospects for HIV therapies. Science, 1993, 260, 1286-1293.
    • (1993) Science , vol.260 , pp. 1286-1293
    • Johnston, M.I.1    Hoth, D.F.2
  • 7
    • 0026771497 scopus 로고
    • 1, 3, 6- Trisubstituted indoles as peptidoleukotriene antagonists: Benefits of a second, polar, pyrrole substituent
    • Brown, F.J.; Cronk, L.A.; Aharony, D.; Snyder, D.W. 1, 3, 6- Trisubstituted indoles as peptidoleukotriene antagonists: benefits of a second, polar, pyrrole substituent. J. Med. Chem., 1992, 35, 2419- 2439.
    • (1992) J. Med. Chem. , vol.35 , pp. 2419-2439
    • Brown, F.J.1    Cronk, L.A.2    Aharony, D.3    Snyder, D.W.4
  • 8
    • 68149103322 scopus 로고    scopus 로고
    • Anti HIV-1 agents 3, Synthesis and in vitro anti-HIV-1 activity of some N-arylsulfonylindoles
    • Fan, L.L.; Liu, W.Q.; Xu, H.; Yang, L.M.; Lv, M.; Zheng, Y.T. Anti HIV-1 agents 3. Synthesis and in vitro anti-HIV-1 activity of some N-arylsulfonylindoles. Chem. Pharm. Bull., 2009, 57, 797- 800.
    • (2009) Chem. Pharm. Bull. , vol.57 , pp. 797-800
    • Fan, L.L.1    Liu, W.Q.2    Xu, H.3    Yang, L.M.4    Lv, M.5    Zheng, Y.T.6
  • 9
    • 0030045677 scopus 로고    scopus 로고
    • 2-Sulfonyl-4-chloroanilino moiety: A potent pharmacophore for the anti-human immunodeficiency virus type 1 activity of pyrrolyl aryl sulfones
    • Marino, A.; Romano, S.; Silvio, M.; Anna, G.L.; Simona, C.; Giovanna, P.; Paolo, L. C. 2-Sulfonyl-4-chloroanilino moiety: A potent pharmacophore for the anti-human immunodeficiency virus type 1 activity of pyrrolyl aryl sulfones. J. Med. Chem., 1996, 39, 522-530.
    • (1996) J. Med. Chem. , vol.39 , pp. 522-530
    • Marino, A.1    Romano, S.2    Silvio, M.3    Anna, G.L.4    Simona, C.5    Giovanna, P.6    Paolo, L.C.7
  • 10
    • 77954219003 scopus 로고    scopus 로고
    • Anti HIV-1 agents 5: Synthesis and anti-HIV-1 activity of some narylsulfonyl- 3-acetylindoles in vitro
    • Ran, J.Q.; Huang, N.; Xu, H.; Yang, L.M.; Lv, M.; Zheng, Y.T. Anti HIV-1 agents 5: Synthesis and anti-HIV-1 activity of some Narylsulfonyl- 3-acetylindoles in vitro. Bioorg. Med. Chem. Lett., 2010, 20, 3534-3536.
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 3534-3536
    • Ran, J.Q.1    Huang, N.2    Xu, H.3    Yang, L.M.4    Lv, M.5    Zheng, Y.T.6
  • 11
    • 26844537941 scopus 로고    scopus 로고
    • 3-1, 3, 4-oxadiazoline: Evidence for a carbonyl ylide intermediate
    • 3-1, 3, 4-oxadiazoline: Evidence for a carbonyl ylide intermediate. J. Org. Chem., 2005, 70, 8431- 8436.
    • (2005) J. Org. Chem. , vol.70 , pp. 8431-8436
    • Czardybon, W.1    Warkentin, J.2    Werstiuk, N.H.3
  • 12
    • 0001599869 scopus 로고    scopus 로고
    • 3-1, 3, 4- oxadiazoline in the presence of DMAD
    • 3-1, 3, 4- oxadiazoline in the presence of DMAD. Org. Lett., 2000, 2, 3501-3503.
    • (2000) Org. Lett. , vol.2 , pp. 3501-3503
    • Lu, X.S.1    Warkentin, J.2
  • 13
    • 57749104658 scopus 로고    scopus 로고
    • 1, 3, 4- Oxadiazoline derivatives as novel potential inhibitors targeting chitin biosynthesis: Design, synthesis and biological evaluation
    • Ke, S.Y.; Liu, F.Y.; Wang, N.; Yang, Q.; Qian, X.H. 1, 3, 4- Oxadiazoline derivatives as novel potential inhibitors targeting chitin biosynthesis: Design, synthesis and biological evaluation. Bioorg. Med. Chem. Lett., 2009, 19, 332-335.
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 332-335
    • Ke, S.Y.1    Liu, F.Y.2    Wang, N.3    Yang, Q.4    Qian, X.H.5
  • 14
    • 37849015593 scopus 로고    scopus 로고
    • Synthesis and characterization of platinum(II) oxadiazoline complexes and their in vitro antitumor activity in platinum-sensitive and -resistant cancer cell lines
    • Coley, H.M.; Sarju, J.; Wagner, G. Synthesis and characterization of platinum(II) oxadiazoline complexes and their in vitro antitumor activity in platinum-sensitive and -resistant cancer cell lines. J. Med. Chem., 2008, 51, 135-141.
    • (2008) J. Med. Chem. , vol.51 , pp. 135-141
    • Coley, H.M.1    Sarju, J.2    Wagner, G.3
  • 15
    • 4444361143 scopus 로고    scopus 로고
    • Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1- adamantyl)-2-substituted thio-1, 3, 4-oxadiazoles and 5-(1- adamantyl)-3- substituted aminomethyl-1, 3, 4-oxadiazoline-2- thiones
    • El-Emam, A.A.; Al-Deeb, O.A.; Al-Omar, M.; Lehmann, J. Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1- adamantyl)-2-substituted thio-1, 3, 4-oxadiazoles and 5-(1- adamantyl)-3-substituted aminomethyl-1, 3, 4-oxadiazoline-2- thiones. Bioorg. Med. Chem., 2004, 12, 5107-5113.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 5107-5113
    • El-Emam, A.A.1    Al-Deeb, O.A.2    Al-Omar, M.3    Lehmann, J.4
  • 16
    • 11844255399 scopus 로고    scopus 로고
    • Bioisosterism: A useful strategy for molecular modification and drug design
    • Lima, L.M.; Barreiro, E.J. Bioisosterism: A useful strategy for molecular modification and drug design. Curr. Med. Chem., 2005, 12, 23-49.
    • (2005) Curr. Med. Chem. , vol.12 , pp. 23-49
    • Lima, L.M.1    Barreiro, E.J.2
  • 17
    • 77954291979 scopus 로고    scopus 로고
    • Anti human immunodeficiency virus type 1 (HIV-1) agents 4. Discovery of 5, 5 -(p-phenylenebisazo)-8-hydroxyquinoline sulfonates as new HIV-1 inhibitors in vitro
    • Zeng, X.W.; Huang, N.; Xu, H.; Yang, L.M.; Qu, H.; Zheng, Y.T. Anti human immunodeficiency virus type 1 (HIV-1) agents 4. Discovery of 5, 5 '-(p-phenylenebisazo)-8-hydroxyquinoline sulfonates as new HIV-1 inhibitors in vitro. Chem. Pharm. Bull., 2010, 58, 976-979.
    • (2010) Chem. Pharm. Bull. , vol.58 , pp. 976-979
    • Zeng, X.W.1    Huang, N.2    Xu, H.3    Yang, L.M.4    Qu, H.5    Zheng, Y.T.6
  • 18
    • 51149107005 scopus 로고    scopus 로고
    • Synthesis of new 4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: A novel class of potential antibacterial and ant tubercular agents
    • Joshi, S.D.; Vagdevi, H.M.; Vaidya, V.P.; Gadaginamath, G.S. Synthesis of new 4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: A novel class of potential antibacterial and antitubercular agents. Eur. J. Med. Chem., 2008, 43, 1989-1996.
    • (2008) Eur. J. Med. Chem. , vol.43 , pp. 1989-1996
    • Joshi, S.D.1    Vagdevi, H.M.2    Vaidya, V.P.3    Gadaginamath, G.S.4
  • 19
    • 39049092070 scopus 로고    scopus 로고
    • New synthesis of pyrazolyl-1, 3, 4-oxadiazole and 1, 3, 4-oxadiazoline derivatives
    • Cottineau, B.; Renaux, S.; Chenault, J.; Guillaumet, G. New synthesis of pyrazolyl-1, 3, 4-oxadiazole and 1, 3, 4-oxadiazoline derivatives. Lett. Org. Chem., 2005, 2, 599-601.
    • (2005) Lett. Org. Chem. , vol.2 , pp. 599-601
    • Cottineau, B.1    Renaux, S.2    Chenault, J.3    Guillaumet, G.4
  • 20
    • 67249164578 scopus 로고    scopus 로고
    • Synthesis of novel 3-acetyl-2-aryl-5- (3-aryl-1-phenyl-pyrazol-4-yl)-2, 3- dihydro-1, 3, 4-oxadiazoles
    • Li, C.K.; Ma, Y.J.; Cao, L.H. Synthesis of novel 3-acetyl-2-aryl-5- (3-aryl-1-phenyl-pyrazol-4-yl)-2, 3- dihydro-1, 3, 4-oxadiazoles. J. Chin. Chem. Soc., 2009, 56, 182-185.
    • (2009) J. Chin. Chem. Soc. , vol.56 , pp. 182-185
    • Li, C.K.1    Ma, Y.J.2    Cao, L.H.3
  • 21
    • 84891727184 scopus 로고    scopus 로고
    • An efficiently sonochemical synthesis of 2-(N-arylsulfonylindol-3-yl)-3- N-acyl-5-phenyl-1, 3, 4- oxadiazolines
    • Xu, H.; Che, Z.P.; Wang, Q. An efficiently sonochemical synthesis of 2-(N-arylsulfonylindol-3-yl)-3-N-acyl-5-phenyl-1, 3, 4- oxadiazolines. Heterocycles, 2010, 82, 825-832.
    • (2010) Heterocycles , vol.82 , pp. 825-832
    • Xu, H.1    Che, Z.P.2    Wang, Q.3
  • 22
    • 80955159780 scopus 로고    scopus 로고
    • Solvent-free, microwave assisted Knoevenagel condensation of novel 2, 5-disubstituted indole analogues and their biological evaluation
    • Biradar, J.S.; Sasidhar, B.S. Solvent-free, microwave assisted Knoevenagel condensation of novel 2, 5-disubstituted indole analogues and their biological evaluation. Eur. J. Med. Chem., 2011, 46, 6112-6118.
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 6112-6118
    • Biradar, J.S.1    Sasidhar, B.S.2
  • 23
    • 79955573819 scopus 로고    scopus 로고
    • Microwave assisted synthesis and structure-activity relationship of 4-hydroxy-N'- [1-phenylethylidene]-2H/2-methyl- 1, 2-benzothiazine-3- carbohydrazide 1, 1-dioxides as anti-microbial agents
    • Ahmad, N.; Zia-ur-Rehman, M.; Siddiqui, H.L.; Ullah, M.F.; Parvez, M. Microwave assisted synthesis and structure-activity relationship of 4-hydroxy-N'- [1-phenylethylidene]-2H/2-methyl- 1, 2-benzothiazine-3- carbohydrazide 1, 1-dioxides as anti-microbial agents. Eur. J. Med. Chem., 2011, 46, 2368-2377.
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 2368-2377
    • Ahmad, N.1    Zia-Ur-Rehman, M.2    Siddiqui, H.L.3    Ullah, M.F.4    Parvez, M.5
  • 24
    • 27844509941 scopus 로고    scopus 로고
    • Microwave-enhanced reaction rates for nanoparticle synthesis
    • Gerbec, J.A.; Magana, D.; Washington, A.; Strouse, G.F. Microwave-enhanced reaction rates for nanoparticle synthesis. J. Am. Chem. Soc., 2005, 127, 15791-15800.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 15791-15800
    • Gerbec, J.A.1    Magana, D.2    Washington, A.3    Strouse, G.F.4
  • 25
    • 25144446828 scopus 로고    scopus 로고
    • Microwave-assisted organic synthesis: Scale-up of palladium catalyzed aminations using single-mode and multi-mode microwave equipment
    • Loones, K.T.J.; Maes, B.U.W.; Rombouts, G.; Hostyn, S.; Diels, G. Microwave-assisted organic synthesis: scale-up of palladiumcatalyzed aminations using single-mode and multi-mode microwave equipment. Tetrahedron, 2005, 61, 10338-10348.
    • (2005) Tetrahedron , vol.61 , pp. 10338-10348
    • Loones, K.T.J.1    Maes, B.U.W.2    Rombouts, G.3    Hostyn, S.4    Diels, G.5
  • 26
    • 84055182866 scopus 로고    scopus 로고
    • A multi-component domino reaction for the direct access to polyfunctionalized indoles via intermolecular allylic esterification and indolation
    • Jiang, B.; Yi, M.; Shi, F.; Tu, S.; Pindi, S.; McDowell, P.; Li, G. A multi-component domino reaction for the direct access to polyfunctionalized indoles via intermolecular allylic esterification and indolation. Chem. Commun., 2012, 48, 808-810.
    • (2012) Chem. Commun. , vol.48 , pp. 808-810
    • Jiang, B.1    Yi, M.2    Shi, F.3    Tu, S.4    Pindi, S.5    McDowell, P.6    Li, G.7
  • 27
    • 84864493012 scopus 로고    scopus 로고
    • Domino constructions of pentacyclic indeno [2, 1-c]quinolines and pyrano [4, 3-b]oxepines by [4+1]/[3+2+1]/[5+1] and [4+3] multiple cyclizations
    • Jiang, B.; Feng, B.; Wang, S.; Tu, S.; Li, G. Domino constructions of pentacyclic indeno [2, 1-c]quinolines and pyrano [4, 3-b]oxepines by [4+1]/[3+2+1]/[5+1] and [4+3] multiple cyclizations. Chem. Eur. J., 2012, 18, 9823-9826.
    • (2012) Chem. Eur. J. , vol.18 , pp. 9823-9826
    • Jiang, B.1    Feng, B.2    Wang, S.3    Tu, S.4    Li, G.5
  • 30
    • 84860565990 scopus 로고    scopus 로고
    • Parallel microwave-assisted synthesis of ionic liquids and screening for denitrogenation of straight-run diesel feed by liquid liquid extraction
    • Ceron, M.A.; Guzman-Lucero, D.J.; Palomeque, J.F.; Martinez- Palou, R. Parallel microwave-assisted synthesis of ionic liquids and screening for denitrogenation of straight-run diesel feed by liquidliquid extraction. Comb. Chem. High Throughput Screen., 2012, 15, 427-432.
    • (2012) Comb. Chem. High Throughput Screen. , vol.15 , pp. 427-432
    • Ceron, M.A.1    Guzman-Lucero, D.J.2    Palomeque, J.F.3    Martinez- Palou, R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.