메뉴 건너뛰기




Volumn 23, Issue 6, 2014, Pages 3187-3199

Studies on the synthesis, in vitro antitumor activity of 4H-benzo[h]chromene, 7H-benzo[h]chromene[2,3-d]pyrimidine derivatives and structure-Activity relationships of the 2-,3- and 2,3-positions

Author keywords

4 Methoxy 1 naphthol; 4H Benzo h chromenes; 7H Benzo h chromeno 2 3 d pyrimidines; Antitumor; SAR; Cyanocinnamonitriles

Indexed keywords

2 AMINO 4 (4 CHLOROPHENYL) 6 METHOXY 4H BENZO[H]CHROMENE 3 CARBONITRILE; 2 AMINOMETHYLENEAMINO 4 (4 CHLOROPHENYL) 6 METHOXY 4H BENZO[H]CHROMENE 3 CARBONITRILE; 2 BENZYLIDENEAMINO 4 (4 CHLOROPHENYL) 6 METHOXY 4H BENZO[H]CHROMENE 3 CARBONITRILE; 2 DIACETYLAMINO 4 (4 CHLOROPHENYL) 6 METHOXY 4H BENZO[H]CHROMENE 3 CARBONITRILE; 2 METHYLAMINOMETHYLENEAMINO 4 (4 CHLOROPHENYL) 6 METHOXY 4H BENZO[H]CHROMENE 3 CARBONITRILE; 4 (4 CHLOROPHENYL) 2 DIMETHYLAMINOMETHYLENEAMINO 6 METHOXY 4H BENZO[H]CHROMENE 3 CARBONITRILE; 4 (4 CHLOROPHENYL) 2 ETHOXYMETHYLENEAMINO 6 METHOXY 4H BENZO[H]CHROMENE 3 CARBONITRILE; 4H BENZO[H]CHROMENE; 7 (4 CHLOROPHENYL) 5 METHOXY 7H,9H BENZO[H]CHROMENO[2,3 D]PYRIMIDIN 8 ONE; 7H BENZO[H]CHROMENE[2,3 D ]PYRIMIDINE DERIVATIVE; 8 AMINO 7 (4 CHLOROPHENYL) 5 METHOXY 7H BENZO[H]CHROMENO[2,3 D]PYRIMIDINE; 9 AMINE 7 (4 CHLOROPHENYL) 5 METHOXY 8 IMINO 7H BENZO[H]CHROMENO[2,3 D]PYRIMIDINE; 9 BENZYLIDENEAMINO 7 (4 CHLOROPHENYL) 5 METHOXY 8 IMINO 7H BENZO[H]CHROMENO[2,3-D]PYRIMIDINE; CHROMENE DERIVATIVE; COLCHICINE; CYTOTOXIC AGENT; DOXORUBICIN; ETHYL 2 AMINO 4 (4 CHLOROPHENYL) 6 METHOXY 4H BENZO[H]CHROMENE 3 CARBOXYALTE; ETHYL 4 (4 CHLOROPHENYL) 2 DIMETHYLAMINOMETHYLENEAMINO 6 METHOXY 4H BENZO[H]CHROMENE 3 CARBOXYLATE; ETHYL 4 (4 CHLOROPHENYL) 2 FORMAMIDO 6 METHOXY 4H BENZO[H]CHROMENE 3 CARBOXYLATE; FUNCTIONAL GROUP; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; VINBLASTINE;

EID: 84898877282     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0904-x     Document Type: Article
Times cited : (63)

References (37)
  • 1
    • 4043158392 scopus 로고    scopus 로고
    • Synthesis of hydroxyquinoline derivatives, aminohydroxychromene, aminocoumarin and their antimicrobial activities
    • 10.3987/COM-04-10089
    • Abd-El-Aziz AS, El-Agrody AM, Bedair AH, Christopher Corkery T, Ata A (2004) Synthesis of hydroxyquinoline derivatives, aminohydroxychromene, aminocoumarin and their antimicrobial activities. Heterocycles 63:1793-1812
    • (2004) Heterocycles , vol.63 , pp. 1793-1812
    • Abd-El-Aziz, A.S.1    El-Agrody, A.M.2    Bedair, A.H.3    Christopher Corkery, T.4    Ata, A.5
  • 3
    • 84860709647 scopus 로고    scopus 로고
    • Synthesis and antitumor activities of 4H-pyrano[3,2-h]quinoline-3- carbonitrile, 7H-pyrimido [4',5':6,5]pyrano[3,2-h]quinoline, and 14H-pyrimido[4',5':6,5]pyrano[3,2-h][1,2,4]triazolo[1,5-c]quinoline derivatives
    • Al-Ghamdi AM, Abd EL-Wahab AHF, Mohamed HM, El-Agrody AM (2012) Synthesis and antitumor activities of 4H-pyrano[3,2-h]quinoline-3-carbonitrile, 7H-pyrimido [4',5':6,5]pyrano[3,2-h]quinoline, and 14H-pyrimido[4',5':6,5] pyrano[3,2-h][1,2,4]triazolo[1,5-c]quinoline derivatives. Lett Drug Des Discov 9:459-470
    • (2012) Lett Drug des Discov , vol.9 , pp. 459-470
    • Al-Ghamdi, A.M.1    Abd El-Wahab, A.H.F.2    Mohamed, H.M.3    El-Agrody, A.M.4
  • 4
    • 84861661062 scopus 로고    scopus 로고
    • Synthesis, characterization and DFT study of 4H-benzo[h]chromene derivatives
    • 10.1016/j.molstruc.2012.03.018
    • Al-Sehemi AG, Irfan A, El-Agrody AM (2012) Synthesis, characterization and DFT study of 4H-benzo[h]chromene derivatives. J Mol Struct 1018:171-175
    • (2012) J Mol Struct , vol.1018 , pp. 171-175
    • Al-Sehemi, A.G.1    Irfan, A.2    El-Agrody, A.M.3
  • 7
    • 0014512931 scopus 로고
    • Researches in the field of antiviral compounds. Mannich bases of 3-hydroxycoumarin
    • 10.1021/jm00303a616
    • Cingolant GM, Pigini M (1969) Researches in the field of antiviral compounds. Mannich bases of 3-hydroxycoumarin. J Med Chem 12:531-532
    • (1969) J Med Chem , vol.12 , pp. 531-532
    • Cingolant, G.M.1    Pigini, M.2
  • 8
    • 84455189156 scopus 로고    scopus 로고
    • Synthesis of certain novel 4H-pyrano[3,2-h]quinoline derivatives
    • 10.3998/ark.5550190.0012.b12
    • El-Agrody AM, Al-Ghamdi AM (2011) Synthesis of certain novel 4H-pyrano[3,2-h]quinoline derivatives. Arkivoc xi:134-146
    • (2011) Arkivoc , vol.11 , pp. 134-146
    • El-Agrody, A.M.1    Al-Ghamdi, A.M.2
  • 9
    • 79956341143 scopus 로고    scopus 로고
    • Synthesis of some new 2-substituted 12H-chromeno[3,2-e][1,2,4]triazolo[1, 5-c]pyrimidine, 3-ethoxycarbonyl-12H-chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine-2-one, ethyl 2-formylamino\acetylamino-4H-chromene-3-carboxylate and some of their antimicrobial activities
    • 10.3184/174751911X12964930076728
    • El-Agrody AM, Sabry NM, Motlaq SS (2011) Synthesis of some new 2-substituted 12H-chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine, 3-ethoxycarbonyl-12H-chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-one, ethyl 2-formylamino\acetylamino-4H-chromene-3-carboxylate and some of their antimicrobial activities. J Chem Res 35:77-83
    • (2011) J Chem Res , vol.35 , pp. 77-83
    • El-Agrody, A.M.1    Sabry, N.M.2    Motlaq, S.S.3
  • 10
    • 84855179452 scopus 로고    scopus 로고
    • Synthesis, antimicrobial and antitumor activities of certain novel 2-Amino-9-(4-halostyryl)-4H-pyrano[3,2-h]-quinoline derivatives
    • 10.1007/s00044-011-9965-x
    • El-Agrody AM, Khattab ESAEH, Fouda AM, Al-Ghamdi AM (2012) Synthesis, antimicrobial and antitumor activities of certain novel 2-Amino-9-(4-halostyryl) -4H-pyrano[3,2-h]-quinoline derivatives. Med Chem Res. doi: 10.1007/s00044-011- 9965-x
    • (2012) Med Chem Res
    • El-Agrody, A.M.1    Khattab, E.2    Fouda, A.M.3    Al-Ghamdi, A.M.4
  • 11
    • 84874114867 scopus 로고    scopus 로고
    • Synthesis, antitumoractivity, and structure-Activity relationship of some 4H-pyrano[3,2-h]quinoline and 7H-pyrimido-[4',5':6,5]pyrano[3,2-h]quinoline derivatives
    • 10.1007/s00044-012-0142-7
    • El-Agrody AM, Abd-Rabboh HSM, Al-Ghamdi AM (2013) Synthesis, antitumoractivity, and structure-Activity relationship of some 4H-pyrano[3,2-h]quinoline and 7H-pyrimido-[4',5':6,5]pyrano[3,2-h]quinoline derivatives. Med Chem Res 22:1339-1355
    • (2013) Med Chem Res , vol.22 , pp. 1339-1355
    • El-Agrody, A.M.1    Abd-Rabboh, H.S.M.2    Al-Ghamdi, A.M.3
  • 12
    • 84898925214 scopus 로고    scopus 로고
    • Microwave assisted synthesis of 2-Amino-6-methoxy-4H-benzo[h]chromene derivatives
    • 10.5155/eurjchem.5.1.133-137.923
    • El-Agrody AM, Al-Anood MA, Fouda AM (2014) Microwave assisted synthesis of 2-Amino-6-methoxy-4H-benzo[h]chromene derivatives. Eur J Med Chem 5:133-137
    • (2014) Eur J Med Chem , vol.5 , pp. 133-137
    • El-Agrody, A.M.1    Al-Anood, M.A.2    Fouda, A.M.3
  • 13
    • 77953201608 scopus 로고    scopus 로고
    • Synthesis and antimicrobial activity of chromone-linked-2-pyridone fused with 1,2,4-triazoles, 1,2,4-triazines and 1,2,4-triazepines ring systems
    • 10.1590/S0103-50532010000600010
    • El-Sayed AT, Ibrahim MA (2010) Synthesis and antimicrobial activity of chromone-linked-2-pyridone fused with 1,2,4-triazoles, 1,2,4-triazines and 1,2,4-triazepines ring systems. J Braz Chem 21:1007-1016
    • (2010) J Braz Chem , vol.21 , pp. 1007-1016
    • El-Sayed, A.T.1    Ibrahim, M.A.2
  • 14
    • 77950037964 scopus 로고    scopus 로고
    • Chromene-3-carboxamide derivatives discovered from virtual screening as potent inhibitors of the tumour maker, AKR1B10
    • 20304656 10.1016/j.bmc.2010.02.050
    • Endo S, Matsunaga T, Kuwata K, Zhao H-T, El-Kabbani O, Kitade Y, Hara A (2010) Chromene-3-carboxamide derivatives discovered from virtual screening as potent inhibitors of the tumour maker, AKR1B10. Bioorg Med Chem 18:2485-2490
    • (2010) Bioorg Med Chem , vol.18 , pp. 2485-2490
    • Endo, S.1    Matsunaga, T.2    Kuwata, K.3    Zhao, H.-T.4    El-Kabbani, O.5    Kitade, Y.6    Hara, A.7
  • 16
    • 0031555345 scopus 로고    scopus 로고
    • DNA strand-breaking activity and mutagenicity of 2,3-dihydro-3,5- dihydroxy-6-methyl-4H-pyran-4-one (DDMP), a Maillard reaction product of glucose and glycine
    • 9465913 10.1016/S1383-5718(97)00141-1
    • Hiramoto K, Nasuhara A, Michiloshi K, KatoT Kikugawa K (1997) DNA strand-breaking activity and mutagenicity of 2,3-dihydro-3,5-dihydroxy-6-methyl- 4H-pyran-4-one (DDMP), a Maillard reaction product of glucose and glycine. Mutat Res 395:47-56
    • (1997) Mutat Res , vol.395 , pp. 47-56
    • Hiramoto, K.1    Nasuhara, A.2    Michiloshi, K.3    Katot, K.K.4
  • 19
    • 34250904254 scopus 로고    scopus 로고
    • Discovery of 4-Aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 3. Structure-Activity relationships of fused rings at the 7,8-positions
    • 17497765 10.1021/jm070216c
    • Kemnitzer W, Drewe J, Jiang S, Zhang H, Zhao J, Crogan-Grundy C, Xu L, Lamothe S, Gourdeau H, Denis R, Tseng B, Kasibhatla S, Cai SX (2007) Discovery of 4-Aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 3. Structure-Activity relationships of fused rings at the 7,8-positions. J Med Chem 50:2858-2864
    • (2007) J Med Chem , vol.50 , pp. 2858-2864
    • Kemnitzer, W.1    Drewe, J.2    Jiang, S.3    Zhang, H.4    Zhao, J.5    Crogan-Grundy, C.6    Xu, L.7    Lamothe, S.8    Gourdeau, H.9    Denis, R.10    Tseng, B.11    Kasibhatla, S.12    Cai, S.X.13
  • 20
    • 39149095977 scopus 로고    scopus 로고
    • Discovery of 4-Aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 4. Structure-Activity relationships of N-Alkyl substituted pyrrole fused at the 7,8-positions
    • 18197614 10.1021/jm7010657
    • Kemnitzer W, Drewe J, Jiang S, Zhang H, Zhao J, Crogan-Grundy C, Labreque D, Dubenick M, Attardo G, Denis R, Lamothe S, Gourdeau H, Tseng B, Kasibhatla S, Cai SX (2008) Discovery of 4-Aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 4. Structure-Activity relationships of N-Alkyl substituted pyrrole fused at the 7,8-positions. J Med Chem 51:417-423
    • (2008) J Med Chem , vol.51 , pp. 417-423
    • Kemnitzer, W.1    Drewe, J.2    Jiang, S.3    Zhang, H.4    Zhao, J.5    Crogan-Grundy, C.6    Labreque, D.7    Dubenick, M.8    Attardo, G.9    Denis, R.10    Lamothe, S.11    Gourdeau, H.12    Tseng, B.13    Kasibhatla, S.14    Cai, S.X.15
  • 21
    • 77950860382 scopus 로고    scopus 로고
    • Analgesic, anti-pyretic and DNA cleavage studies of novel pyrimidine derivatives of coumarin moiety
    • 20356657 10.1016/j.ejmech.2010.02.048
    • Keri RS, Hosamani KM, Shingalapur RV, Hugar MH (2010) Analgesic, anti-pyretic and DNA cleavage studies of novel pyrimidine derivatives of coumarin moiety. Eur J Med Chem 45:2597-2605
    • (2010) Eur J Med Chem , vol.45 , pp. 2597-2605
    • Keri, R.S.1    Hosamani, K.M.2    Shingalapur, R.V.3    Hugar, M.H.4
  • 22
    • 0033539161 scopus 로고    scopus 로고
    • Design, synthesis, and evaluation of chromen-2-ones as potent and selective human dopamine D4 antagonists
    • 10479303 10.1021/jm990266k
    • Kesten SR, Heffner TG, Johnson SJ, Pugsley TA, Wright JL, Wise DL (1999) Design, synthesis, and evaluation of chromen-2-ones as potent and selective human dopamine D4 antagonists. J Med Chem 42:3718-3725
    • (1999) J Med Chem , vol.42 , pp. 3718-3725
    • Kesten, S.R.1    Heffner, T.G.2    Johnson, S.J.3    Pugsley, T.A.4    Wright, J.L.5    Wise, D.L.6
  • 23
    • 0036754283 scopus 로고    scopus 로고
    • Synthesis of halogen derivatives of benzo[h]cheromene and benzo[a]anthracene with promising antimicrobial activities
    • 12385521 10.1016/S0014-827X(02)01263-6
    • Khafagy MM, Abd El-Wahab AHF, Eid FA, El-Agrody AM (2002) Synthesis of halogen derivatives of benzo[h]cheromene and benzo[a]anthracene with promising antimicrobial activities. IL Farmaco 57:715-722
    • (2002) IL Farmaco , vol.57 , pp. 715-722
    • Khafagy, M.M.1    Abd El-Wahab, A.H.F.2    Eid, F.A.3    El-Agrody, A.M.4
  • 24
    • 77957852160 scopus 로고    scopus 로고
    • Aqua mediated synthesis of 2-Amino-6-benzothiazol-2-ylsulfanyl-chromenes and its in vitro study, explanation of the structure-Activity relationships (SARs) as antibacterial agent
    • 20810191 10.1016/j.ejmech.2010.08.010
    • Kidwai M, Poddar R, Bhardwaj S, Singh S, Mehta LP (2010) Aqua mediated synthesis of 2-Amino-6-benzothiazol-2-ylsulfanyl-chromenes and its in vitro study, explanation of the structure-Activity relationships (SARs) as antibacterial agent. Eur J Med Chem 45:5031-5038
    • (2010) Eur J Med Chem , vol.45 , pp. 5031-5038
    • Kidwai, M.1    Poddar, R.2    Bhardwaj, S.3    Singh, S.4    Mehta, L.P.5
  • 25
    • 31344477940 scopus 로고    scopus 로고
    • Effects of DK-002, a synthesized (6aS, cis)-9,10-dimethoxy-7,11b-dihydro- indeno[2,1-c]chromene-3,6a-diol, on platelet activity
    • 16153663 10.1016/j.lfs.2005.06.017
    • Lee K-S, Khil L-Y, Chae S-H, Kim D, Lee B-H, Hwang G-S, Moon C-H, Chang T-S, Moon C-K (2006) Effects of DK-002, a synthesized (6aS, cis)-9,10-dimethoxy- 7,11b-dihydro-indeno[2,1-c]chromene-3,6a-diol, on platelet activity. Life Sci 78:1091-1097
    • (2006) Life Sci , vol.78 , pp. 1091-1097
    • Lee, K.-S.1    Khil, L.-Y.2    Chae, S.-H.3    Kim, D.4    Lee, B.-H.5    Hwang, G.-S.6    Moon, C.-H.7    Chang, T.-S.8    Moon, C.-K.9
  • 28
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays
    • 10.1016/0022-1759(83)90303-4
    • Mossman T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55-63
    • (1983) J Immunol Methods , vol.65 , pp. 55-63
    • Mossman, T.1
  • 30
    • 79151483231 scopus 로고    scopus 로고
    • Synthesis of 4H-chromene, coumarin, 12H-chromeno[2,3-d]pyrimidine derivatives and some of their antimicrobial and cytotoxicity activities
    • 21216502 10.1016/j.ejmech.2010.12.015
    • Sabry NM, Mohamed HM, Khattab Essam Shawky AEH, Motlaq SS, El-Agrody AM (2011) Synthesis of 4H-chromene, coumarin, 12H-chromeno[2,3-d]pyrimidine derivatives and some of their antimicrobial and cytotoxicity activities. Eur J Med Chem 46:765-772
    • (2011) Eur J Med Chem , vol.46 , pp. 765-772
    • Sabry, N.M.1    Mohamed, H.M.2    Khattab Essam Shawky, A.E.H.3    Motlaq, S.S.4    El-Agrody, A.M.5
  • 31
    • 80054755763 scopus 로고    scopus 로고
    • Discovery and synthesis of novel substituted benzocoumarins as orally active lipid modulating agents
    • 21983443 10.1016/j.bmcl.2011.09.053
    • Sashidhara KV, Kumar M, Modukuri RK, Srivastava A, Puri A (2011) Discovery and synthesis of novel substituted benzocoumarins as orally active lipid modulating agents. Bioorg Med Chem Lett 21:6709-6713
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 6709-6713
    • Sashidhara, K.V.1    Kumar, M.2    Modukuri, R.K.3    Srivastava, A.4    Puri, A.5
  • 32
    • 77950864682 scopus 로고    scopus 로고
    • Novel 3-Alkanoyl/aroyl/-heteroaroyl-2H-chromene-2-thiones: Synthesis and evaluation of their antioxidant activities
    • 20170989 10.1016/j.ejmech.2010.01.070
    • Singh OM, Devi NS, Thokchom DS, Sharma GJ (2010) Novel 3-Alkanoyl/aroyl/-heteroaroyl-2H-chromene-2-thiones: synthesis and evaluation of their antioxidant activities. Eur J Med Chem 45:2250-2257
    • (2010) Eur J Med Chem , vol.45 , pp. 2250-2257
    • Singh, O.M.1    Devi, N.S.2    Thokchom, D.S.3    Sharma, G.J.4
  • 37
    • 75049086152 scopus 로고    scopus 로고
    • Substituted imino and amino derivatives of 4-hydroxycoumarins as novel antioxidant, antibacterial and antifungal agents: Synthesis and in vitro assessments
    • 10.1016/j.foodchem.2009.11.040
    • Vukovic N, Sukdolak S, Solujic S, Niciforovic N (2010) Substituted imino and amino derivatives of 4-hydroxycoumarins as novel antioxidant, antibacterial and antifungal agents: synthesis and in vitro assessments. Food Chem 120:1011-1018
    • (2010) Food Chem , vol.120 , pp. 1011-1018
    • Vukovic, N.1    Sukdolak, S.2    Solujic, S.3    Niciforovic, N.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.