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Volumn 9, Issue 2, 2013, Pages 177-192

Synthesis of benzopyran linked pyrrolo[2,1-c][1,4]benzodiazepines as DNA-binding and potential anticancer agents

Author keywords

2,2 dimethyl benzopyran; Cytotoxicity; DNA binding affinity; Pyrrolo 2 1 c 1 4 benzodiazepines and piperazine

Indexed keywords

1,2,3,11A TETRAHYDRO 8 HYDROXY 7 METHOXY 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 2,2,8,8 TETRAMETHYL 2H,8H PYRANO[3,2 G]CHROMEN 5 OL; 5 HYDROXY 2,2,8,8 TETRAMETHYL 3,4,7,8 TETRAHYDRO 2H,6H PYRANO[3,2 G]CHROMENE 4,6 DIONE; 6 (3 BROMOPROPOXY) 7 METHOXY 2,2 DIMETHYL 2H CHROMENE; 6 (3 BROMOPROPOXY) 7 METHOXY 2,2 DIMETHYL 4 CHROMANONE; 6 (4 BROMOBUTOXY) 7 METHOXY 2,2 DIMETHYL 2H CHROMENE; 6 (4 BROMOBUTOXY) 7 METHOXY 2,2 DIMETHYL 4 CHROMANONE; 7 METHOXY 2,2 DIMETHYL 2H 6 CHROMENYL)OXY]BUTYLPIPERAZINE; 7 METHOXY 2,2 DIMETHYL 2H 6 CHROMENYL)OXY]PENTYLPIPERAZINE; 7 METHOXY 2,2 DIMETHYL 2H 6 CHROMENYL)OXY]PROPYLPIPERAZINE; 7 METHOXY 8 [3 [7 METHOXY 2,2 DIMETHYL 2H 6 CHROMENYL)OXY]PROPYLOXY] (11AS) 1,2,3, 11A TETRAHYDRO 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 7 METHOXY 8 [4 [7 METHOXY 2,2 DIMETHYL 2H 6 CHROMENYL)OXY]PROPYLOXY] (11AS) 1,2,3, 11A TETRAHYDRO 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 7 METHOXY 8 [5 [7 METHOXY 2,2 DIMETHYL 2H 6 CHROMENYL)OXY]PROPYLOXY] (11AS) 1,2,3, 11A TETRAHYDRO 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; ANTINEOPLASTIC AGENT; BENZOPYRAN DERIVATIVE; N (4 HYDROXY) 5 METHOXY 2 NITROBENZOYL)PYRROLIDINE 2 CARBOXALDEHYDEDIET HYLTHIOACETAL; N [4 (3 BROMOPROPYL)OXY 5 METHOXY 2 NITROBENZOYL]PYRROLIDINE 2 CARBOXALDEHYDE DIETHYLTHIOACETAL; N [4 (4 BROMOBUTYL)OXY 5 METHOXY 2 NITROBENZOYL]PYRROLIDINE 2 CARBOXALDEHYDE DIETHYLTHIOACETAL; N [4 (5 BROMOPENTYL)OXY 5 METHOXY 2 NITROBENZOYL]PYRROLIDINE 2 CARBOXALDEHYDE DIETHYLTHIOACETAL; N [4 [4 (2,2,8,8 TETRAMETHYL 2H,8H PYRANO[3,2 G]CHROMEN 5 YL)OXY]BUTYLOXY 5 METHOXY 2 NITROBENZOYL]PYRROLIDINE 2 CARBOXALDEHYDEDIETHYLTHIOACETAL; N [4 [5 (2,2,8,8 TETRAMETHYL 2H,8H PYRANO[3,2 G]CHROMEN 5 YL)OXY]BUTYLOXY 5 METHOXY 2 NITROBENZOYL]PYRROLIDINE 2 CARBOXALDEHYDEDIETHYLTHIOACETAL; PHLOROGLUCINOL; PYRROLO[2,1 C][1,4]BENZODIAZEPINE DERIVATIVE; TERT BUTYL 4 [3 (2,2,8,8 TETRAMETHYL 2H,8H PYRANO[3,2 G]CHROMEN 5 YL)OXY]PROPYL 1 PIPERAZINECARBOXYLATE; TERT BUTYL 4 [3 (7 METHOXY 2,2 DIMETHYL 2H 6 CHROMENYL)OXY]PROPYL 1 PIPERAZINE CARBOXYLATE; TERT BUTYL 4 [4 (2,2,8,8 TETRAMETHYL 2H,8H PYRANO[3,2 G]CHROMEN 5 YL)OXY]BUTYL 1 PIPERAZINECARBOXYLATE; TERT BUTYL 4 [4 (7 METHOXY 2,2 DIMETHYL 2H 6 CHROMENYL)OXY]PROPYL 1 PIPERAZINE CARBOXYLATE; TERT BUTYL 4 [5 (2,2,8,8 TETRAMETHYL 2H,8H PYRANO[3,2 G]CHROMEN 5 YL)OXY]PENTYL 1 PIPERAZINECARBOXYLATE; TERT BUTYL 4 [5 (7 METHOXY 2,2 DIMETHYL 2H 6 CHROMENYL)OXY]PROPYL 1 PIPERAZINE CARBOXYLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 84877974476     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/1573406411309020003     Document Type: Article
Times cited : (2)

References (32)
  • 1
    • 0035282633 scopus 로고    scopus 로고
    • Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNAinteractive agent with highly efficient cross-linking ability and potent cytotoxicity
    • Gregson, S. J.; Howard, P. W.; Hartley, J. A.; Brooks, N. A.; Adams, L. J.; Jenkins, T. C.; Kelland, L. R.; Thurston, D. E: design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNAinteractive agent with highly efficient cross-linking ability and potent cytotoxicity. J. Med. Chem., 2001, 44, 737-48.
    • (2001) J. Med. Chem. , vol.44 , pp. 737-748
    • Gregson, S.J.1    Howard, P.W.2    Hartley, J.A.3    Brooks, N.A.4    Adams, L.J.5    Jenkins, T.C.6    Kelland, L.R.7    Thurston, D.E.8
  • 2
    • 0022552540 scopus 로고
    • DNA sequence specificity of the pyrrolo[2, 1- c][1, 4]benzodiazepine antitumor antibiotics, Methidiumpropyl- EDTAIron(II) footprinting analysis of DNA binding sites for anthramycin and related drugs
    • Hertzberg, R. P.; Hecht, S. M.; Reynolds, V. L.; Molineux, I. J.; Hurley, L. H: DNA sequence specificity of the pyrrolo[2, 1- c][1, 4]benzodiazepine antitumor antibiotics. Methidiumpropyl- EDTAIron(II) footprinting analysis of DNA binding sites for anthramycin and related drugs. Biochemistry., 1986, 25, 1249-58.
    • (1986) Biochemistry , vol.25 , pp. 1249-1258
    • Hertzberg, R.P.1    Hecht, S.M.2    Reynolds, V.L.3    Molineux, I.J.4    Hurley, L.H.5
  • 4
    • 0025208272 scopus 로고
    • Odebenzylation of a pyrrolo[2, 1-c][1, 4]benzodiazepine in the presence of a carbinolamine functionality: Synthesis of DC-81
    • Thurston, D.E.; Murthy, V. S.; Langley, D. R.; Jones, G. B: Odebenzylation of a pyrrolo[2, 1-c][1, 4]benzodiazepine in the presence of a carbinolamine functionality: synthesis of DC-81. Synthesis., 1990, 1, 81-4.
    • (1990) Synthesis , vol.1 , pp. 81-84
    • Thurston, D.E.1    Murthy, V.S.2    Langley, D.R.3    Jones, G.B.4
  • 5
    • 0026515220 scopus 로고
    • Synthesis, DNA-binding and cytotoxicity of DC-81
    • Bose, D. S.; Jones, G. B.; Thurston, D. E: Synthesis, DNA-Binding and Cytotoxicity of DC-81, Tetrahedron., 1992, 48, 751-8.
    • (1992) Tetrahedron , vol.48 , pp. 751-758
    • Bose, D.S.1    Jones, G.B.2    Thurston, D.E.3
  • 7
    • 70349743960 scopus 로고    scopus 로고
    • Structure-activity relationships of monomeric C2-aryl pyrrolo[2, 1-c][1, 4]benzodiazepine (PBD) antitumor agent the pyrrolobenzodiazepine dimer SJG-136 forms sequence dependent intrastrand DNA cross-links and monoalkylated adducts in addition to inter strand cross-links
    • Rahman, K. M.; Thompson, A. S.; James, C. H.; Narayanaswamy, M.; Thurston, D. E: structure-activity relationships of monomeric C2-aryl pyrrolo[2, 1-c][1, 4]benzodiazepine (PBD) antitumor agent the pyrrolobenzodiazepine dimer SJG-136 forms sequencedependent intrastrand DNA cross-links and monoalkylated adducts in addition to interstrandcross-links. J. Am. Chem. Soc., 2009, 131, 13756-66.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 13756-13766
    • Rahman, K.M.1    Thompson, A.S.2    James, C.H.3    Narayanaswamy, M.4    Thurston, D.E.5
  • 8
    • 73149096027 scopus 로고    scopus 로고
    • Solution structure of a covalently bound pyrrolo[2, 1- c][1, 4]benzodiazepine-benzimidazole hybrid to a 10mer DNA duplex
    • Rettig, M.; Weingarth, M.; Langel, W.; Kamal, A.; Kumar, P. P.; Weisz, K: solution structure of a covalently bound pyrrolo[2, 1- c][1, 4]benzodiazepine-benzimidazole hybrid to a 10mer DNA duplex. Biochemistry., 2009, 48, 12223-32.
    • (2009) Biochemistry , vol.48 , pp. 12223-12232
    • Rettig, M.1    Weingarth, M.2    Langel, W.3    Kamal, A.4    Kumar, P.P.5    Weisz, K.6
  • 9
    • 0141851816 scopus 로고    scopus 로고
    • Design and synthesis of novel chrysene-linked pyrrolo[ 2, 1-c][1, 4]-benzodiazepine hybrids as potential DNA-binding agents
    • Kamal, A.; Ramesh, G.; Ramulu, P.; Srinivas, O. Rehana, T. Sheelu, G: design and synthesis of novel chrysene-linked pyrrolo[ 2, 1-c][1, 4]-benzodiazepine hybrids as potential DNA-binding agents. Bioorg. Med. Chem. Lett., 2003, 13, 3451-4.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 3451-3454
    • Kamal, A.1    Ramesh, G.2    Ramulu, P.3    Srinivas, O.4    Rehana, T.5    Sheelu, G.6
  • 10
    • 0037057577 scopus 로고    scopus 로고
    • Design, synthesis, and evaluation of new noncross-linking pyrrolobenzodiazepine dimers with efficient DNA binding ability and potent antitumor activity
    • Kamal, A.; Ramesh, G.; Laxman, N.; Ramulu, P.; Srinivas, O.; Neelima, K., Kondapi, A. K.; Srinu, V. B.; Nagarajaram, H. M: design, synthesis, and evaluation of new noncross-linking pyrrolobenzodiazepine dimers with efficient DNA binding ability and potent antitumor activity. J. Med. Chem., 2002, 45, 4679-88.
    • (2002) J. Med. Chem. , vol.45 , pp. 4679-4688
    • Kamal, A.1    Ramesh, G.2    Laxman, N.3    Ramulu, P.4    Srinivas, O.5    Neelima, K.6    Kondapi, A.K.7    Srinu, V.B.8    Nagarajaram, H.M.9
  • 11
    • 4644316457 scopus 로고    scopus 로고
    • SJG-136 (NSC 694501), a novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumour activity: Part 2: Efficacy evaluations
    • Alley, M. C.; Hollingshead, M. G.; Pacula-Cox, C. M.; Waud, W. R.; Hartley, J. A.; Howard, P. W.; Gregson, S. J.; Thurston, D. E.; Sausville, E. A: SJG-136 (NSC 694501), a novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumour activity: Part 2: efficacy evaluations. Cancer Res., 2004, 64, 6700-06.
    • (2004) Cancer Res. , vol.64 , pp. 6700-6706
    • Alley, M.C.1    Hollingshead, M.G.2    Pacula-Cox, C.M.3    Waud, W.R.4    Hartley, J.A.5    Howard, P.W.6    Gregson, S.J.7    Thurston, D.E.8    Sausville, E.A.9
  • 12
    • 0141851816 scopus 로고    scopus 로고
    • Design and synthesis of novel chrysene-linked pyrrolo[ 2, 1-c][1, 4]-benzodiazepine hybrids as potential DNA-binding agents
    • Kamal, A.; Ramesh, G.; Ramulu, P.; Srinivas, O. Rehana, T. Sheelu, G: design and synthesis of novel chrysene-linked pyrrolo[ 2, 1-c][1, 4]-benzodiazepine hybrids as potential DNA-binding agents. Bioorg. Med. Chem. Lett., 2003, 13, 3451-4.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 3451-3454
    • Kamal, A.1    Ramesh, G.2    Ramulu, P.3    Srinivas, O.4    Rehana, T.5    Sheelu, G.6
  • 13
    • 34548563728 scopus 로고    scopus 로고
    • 1, 2, 4-benzothiadiazine linked pyrrolo[2, 1-c][1, 4]benzodiazepine conjugates: Synthesis, DNA-binding affinity and cytotoxicity
    • Kamal, A.; Khan, M. N. A.; Reddy, K. S.; Ahmed, S. K.; Kumar, M. S.; Juvekar, A.; Sen, S.; Zingde, S: 1, 2, 4-benzothiadiazine linked pyrrolo[2, 1-c][1, 4]benzodiazepine conjugates: synthesis, DNA-binding affinity and cytotoxicity. Bioorg. Med. Chem. Lett., 2007, 19, 5345-8.
    • (2007) Bioorg. Med. Chem. Lett. , vol.19 , pp. 5345-5348
    • Kamal, A.1    Khan, M.N.A.2    Reddy, K.S.3    Ahmed, S.K.4    Kumar, M.S.5    Juvekar, A.6    Sen, S.7    Zingde, S.8
  • 15
    • 0034684186 scopus 로고    scopus 로고
    • Natural product-like combinatorial libraries based on privileged structures. 3. The libraries from libraries principle for diversity enhancement of benzopyran libraries
    • Nicolaou, K. C.; Pfefferkorn, J. A.; Barluenga, S.; Mitchell, H. J.; Roecker, A. J.; Cao, G. Q: natural product-like combinatorial libraries based on privileged structures. 3. The libraries from libraries principle for diversity enhancement of benzopyran libraries. J. Am. Chem. Soc., 2000, 122, 9968-76.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 9968-9976
    • Nicolaou, K.C.1    Pfefferkorn, J.A.2    Barluenga, S.3    Mitchell, H.J.4    Roecker, A.J.5    Cao, G.Q.6
  • 19
  • 20
    • 0032584097 scopus 로고    scopus 로고
    • Anticancer action of cube insecticide: Correlation for rotenoid constituents between inhibition of NADH: Ubiquinone oxidored uctase and induced ornithine decarboxylase activities
    • Fang, N.; Casida, J. E: anticancer action of cube insecticide: correlation for rotenoid constituents between inhibition of NADH: ubiquinone oxidored uctase and induced ornithine decarboxylase activities. Proc Natl Acad Sci USA., 1998, 95, 3380-4.
    • (1998) Proc Natl Acad Sci USA , vol.95 , pp. 3380-3384
    • Fang, N.1    Casida, J.E.2
  • 22
    • 0034684250 scopus 로고    scopus 로고
    • Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid- phase synthesis of benzopyrans
    • Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G. Q.; Barluenga, S.; Mitchell, H. J: natural product-like combinatorial libraries based on privileged structures. 1. general principles and solid- phase synthesis of benzopyrans. J. Am. Chem. Soc., 2000, 122, 9939-53.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 9939-9953
    • Nicolaou, K.C.1    Pfefferkorn, J.A.2    Roecker, A.J.3    Cao, G.Q.4    Barluenga, S.5    Mitchell, H.J.6
  • 23
    • 0034684186 scopus 로고    scopus 로고
    • Natural product-like combinatorial libraries based on privileged structures. 3. The libraries from libraries principle for diversity enhancement of benzopyran libraries
    • Nicolaou, K. C.; Pfefferkorn, J. A.; Barluenga, S.; Mitchell, H. J.; Roecker, A. J.; Cao, G. Q: natural product-like combinatorial libraries based on privileged structures. 3. The libraries from libraries principle for diversity enhancement of benzopyran libraries. J. Am. Chem. Soc., 2000, 122, 9968-76.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 9968-9976
    • Nicolaou, K.C.1    Pfefferkorn, J.A.2    Barluenga, S.3    Mitchell, H.J.4    Roecker, A.J.5    Cao, G.Q.6
  • 24
    • 3242809006 scopus 로고    scopus 로고
    • Synthesis and DNA binding affinity of novel A-C8/C-C2-exo unsaturated alkoxyamido-linked pyrrolo[2, 1-c][1, 4]benzodiazepine dimers
    • Kamal, A.; Srinivas, O.; Ramulu, P.; Kumar, P. P.; Kumar, S. M.: synthesis and DNA binding affinity of novel A-C8/C-C2-exo unsaturated alkoxyamido-linked pyrrolo[2, 1-c][1, 4]benzodiazepine dimers. Bioorg. Med. Chem., 2004, 12, 4337-4350.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 4337-4350
    • Kamal, A.1    Srinivas, O.2    Ramulu, P.3    Kumar, P.P.4    Kumar, S.M.5
  • 25
    • 60049086079 scopus 로고    scopus 로고
    • Remarkable enhancement in the DNA-binding ability of C2-fluoro substituted pyrrolo[ 2, 1-c][1, 4]benzodiazepines and their anticancer potential
    • Kamal, A.; Rajender, R.; Reddy, D. R.; Reddy, M. K.; Balakishan, G.; Shaik, B. T.; Chourasia, M.; Sastry, N. G.: remarkable enhancement in the DNA-binding ability of C2-fluoro substituted pyrrolo[ 2, 1-c][1, 4]benzodiazepines and their anticancer potential. Bioorg. Med. Chem., 2009, 17, 1557-1572.
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 1557-1572
    • Kamal, A.1    Rajender, R.2    Reddy, D.R.3    Reddy, M.K.4    Balakishan, G.5    Shaik, B.T.6    Chourasia, M.7    Sastry, N.G.8
  • 26
    • 0029133981 scopus 로고
    • Bisimidazoacridones and related compounds: New antineoplastic agents with high selectivity against colon tumors
    • Cholody, W. M.; Hernandez, L.; Hassner, L.; Scudiero, D. A.; Djurickovic, D. B.; Michejda, C. J: bisimidazoacridones and related compounds: new antineoplastic agents with high selectivity against colon tumors. J. Med. Chem., 1995, 38, 3043-52.
    • (1995) J. Med. Chem. , vol.38 , pp. 3043-3052
    • Cholody, W.M.1    Hernandez, L.2    Hassner, L.3    Scudiero, D.A.4    Djurickovic, D.B.5    Michejda, C.J.6
  • 27
    • 0037025442 scopus 로고    scopus 로고
    • Synthesis of C-8 alkylamino substituted pyrrolo[2, 1- c][1, 4]benzodiazepines as potential anticancer agents
    • Kamal, A.; Laxman, N.; Ramesh, G.; Srinivas, O.; Ramulu, P: synthesis of C-8 alkylamino substituted pyrrolo[2, 1- c][1, 4]benzodiazepines as potential anticancer agents. Bioorg Med Chem Let., 2002, 12, 1917-19.
    • (2002) Bioorg Med Chem Let , vol.12 , pp. 1917-1919
    • Kamal, A.1    Laxman, N.2    Ramesh, G.3    Srinivas, O.4    Ramulu, P.5
  • 28
    • 28844445682 scopus 로고    scopus 로고
    • DNA binding potential and cytotoxicity of newly designed pyrrolobenzodiazepine dimers linked through a piperazine side-armed-alkane spacer
    • Kamal, A.; Reddy, P. S. M. M.; Reddy, D. R.; Laxman, E: DNA binding potential and cytotoxicity of newly designed pyrrolobenzodiazepine dimers linked through a piperazine side-armed-alkane spacer. Bioorg. Med. Chem., 2006, 14, 385-94.
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 385-394
    • Kamal, A.1    Reddy, P.S.M.M.2    Reddy, D.R.3    Laxman, E.4
  • 29
    • 0000143411 scopus 로고
    • Synthesis of DNA-interactive pyrrolo[ 2, 1-c][1, 4]benzodiazepines
    • Thurston, D. E.; Bose, D. S: synthesis of DNA-interactive pyrrolo[ 2, 1-c][1, 4]benzodiazepines. Chem Rev., 1994, 94, 433-65.
    • (1994) Chem Rev. , vol.94 , pp. 433-465
    • Thurston, D.E.1    Bose, D.S.2
  • 30
    • 0036083053 scopus 로고    scopus 로고
    • K: Recent developments in the design, synthesis and structure-activity relationship studies of pyrrolo[2, 1-c][1, 4]benzodiazepines as DNA interactive antitumor antibiotics
    • Kamal, A.; Rao, M. V.; Laxman, N.; Ramesh, G.; Reddy, G. S. K: recent developments in the design, synthesis and structure-activity relationship studies of pyrrolo[2, 1-c][1, 4]benzodiazepines as DNAinteractive antitumour antibiotics. Curr. Med. Chem Anti-Cancer Agents., 2002, 2, 215-54.
    • (2002) Curr. Med. Chem Anti-Cancer Agents. , vol.2 , pp. 215-254
    • Kamal, A.1    Rao, M.V.2    Laxman, N.3    Ramesh, G.4    Reddy, G.S.5
  • 31
    • 0343611331 scopus 로고
    • Improved preparation of precocene II, Unexpected results in the reduction of alkoxy substituted acetophenones and 4-chromanones with sodium borohydride
    • Teixidor, P.; Camps, F.; messeguer, A. improved preparation of precocene II. unexpected results in the reduction of alkoxy substituted acetophenones and 4-chromanones with sodium borohydride. Heterocycles., 1988, 27, 2459-65.
    • (1988) Heterocycles , vol.27 , pp. 2459-2465
    • Teixidor, P.1    Camps, F.2    Messeguer, A.3
  • 32
    • 0006297234 scopus 로고    scopus 로고
    • Selective synthesis of analogues of the natural precocenes, synthesis and regioselective (alkylation of 6-chloroand 6-tert-butyl-7, 8-dihyedroxy-2, 2-dimethyl-4-chromanones
    • Sebok, P.; Timar, T: selective synthesis of analogues of the natural precocenes, synthesis and regioselective (alkylation of 6-chloroand 6-tert-butyl-7, 8-dihyedroxy-2, 2-dimethyl-4-chromanones. Heterocycles., 1998, 27, 2595-2607.
    • (1998) Heterocycles , vol.27 , pp. 2595-2607
    • Sebok, P.1    Timar, T.2


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