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Volumn 9, Issue 19, 1999, Pages 2789-2794

Bifunctional 2-naphthyl propargylic sulfones exhibiting high DNA intercalating and alkylating activity

Author keywords

Antitumour compds; DNA; Substituent effects

Indexed keywords

2 NAPHTHYL PROPARGYLIC SULFONE; INTERCALATING AGENT; NAPHTHYL GROUP; SULFONE; UNCLASSIFIED DRUG;

EID: 0033523623     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00475-8     Document Type: Article
Times cited : (11)

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    • 6. For other related studies on propargylic sulfones, see: (a) Sakai, Y.; Bando, Y.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1992, 33, 957. (b) Toshima, K.; Ohta, K.; Ohtsuka, A.; Matsumura, S.; Nakata, M. J. Chem. Soc., Chem. Commun. 1993, 1406. (c) Kerwin, S. M. Tetrahedron Lett. 1994, 35, 1023. (d) Basak, A.; Khamrai, U. K. Tetrahedron Lett. 1995, 36, 7913. (e) Wu, M.-J.; Lin, C.-F.; Wu, J.-S.; Chen, H.-T. Tetrahedron Lett. 1994, 35, 1879. (f) Wu, M.-J.; Lin, C.-F.; Ong, C.-W. BioMed. Chem. Lett. 1996, 6, 675. (g) Wu, M.-J.; Lin, C.-F.; Chen, H.-T.; Duh, T.-H.; Wang, S.-S.; Hsu, S.-C. BioMed. Chem. Lett. 1996, 6, 2183. (h) Lin, C.-F.; Wu, M.-J. J. Org. Chem. 1997, 62, 4546. (i) Grissom, J. W.; Klingberg, D. Tetrahedron Lett. 1995, 36, 6607. (j) Cao, D.; Kolshorn, H.; Meier, H. Tetrahedron Lett. 1995, 36, 7069.
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    • 6. For other related studies on propargylic sulfones, see: (a) Sakai, Y.; Bando, Y.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1992, 33, 957. (b) Toshima, K.; Ohta, K.; Ohtsuka, A.; Matsumura, S.; Nakata, M. J. Chem. Soc., Chem. Commun. 1993, 1406. (c) Kerwin, S. M. Tetrahedron Lett. 1994, 35, 1023. (d) Basak, A.; Khamrai, U. K. Tetrahedron Lett. 1995, 36, 7913. (e) Wu, M.-J.; Lin, C.-F.; Wu, J.-S.; Chen, H.-T. Tetrahedron Lett. 1994, 35, 1879. (f) Wu, M.-J.; Lin, C.-F.; Ong, C.-W. BioMed. Chem. Lett. 1996, 6, 675. (g) Wu, M.-J.; Lin, C.-F.; Chen, H.-T.; Duh, T.-H.; Wang, S.-S.; Hsu, S.-C. BioMed. Chem. Lett. 1996, 6, 2183. (h) Lin, C.-F.; Wu, M.-J. J. Org. Chem. 1997, 62, 4546. (i) Grissom, J. W.; Klingberg, D. Tetrahedron Lett. 1995, 36, 6607. (j) Cao, D.; Kolshorn, H.; Meier, H. Tetrahedron Lett. 1995, 36, 7069.
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    • 2-Naphthyl propargyl sulfide 5 was synthesized from 2-naphthalenethiol and the mesylate of propargyl alcohol in 89% yield (NaH, THF, 0-20 °C, 1 h)
    • 7. 2-Naphthyl propargyl sulfide 5 was synthesized from 2-naphthalenethiol and the mesylate of propargyl alcohol in 89% yield (NaH, THF, 0-20 °C, 1 h).
  • 24
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    • c refer to as the sample and control, respectively
    • c refer to as the sample and control, respectively.
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    • 70 value is defined as the concentration that causes cleavage of 70% Form I DNA
    • 70 value is defined as the concentration that causes cleavage of 70% Form I DNA.
  • 26
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    • All measurements were done in the buffer solution containing 5% DMSO
    • 10. Strothkamp, K. G.; Stromkamp, R. E. J. Che. Edu. 1994, 71, 77. All measurements were done in the buffer solution containing 5% DMSO.
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    • ΦX174 RFI DNA (54.3 μM/bp) was treated with 10 μM ethidium bromide for 2 h before incubation. Conditions for experiments using the EB-pre-teeated DNA are the same as those given in Figure 3
    • 11. ΦX174 RFI DNA (54.3 μM/bp) was treated with 10 μM ethidium bromide for 2 h before incubation. Conditions for experiments using the EB-pre-teeated DNA are the same as those given in Figure 3.


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