publication . Other literature type . Article . 2004

The Synthesis of Dicationic Extended Bis-Benzimidazoles

Kang, Zhijan; Dykstra, Christine C.; Boykin, David W;
Open Access English
  • Published: 28 Feb 2004 Journal: Molecules (issn: 1420-3049, Copyright policy)
  • Publisher: MDPI AG
Abstract
The synthesis of extended dicationic bis-benzimidazoles starting from trans‑1,2-bis(4-cyanophenyl)ethene and trans‑1,2-bis(4-cyanophenyl)cyclopropane is reported. The target diamidines show significant in vitro activity against B. subtilis.
Subjects
free text keywords: amidines, DIBAL reduction, Organic chemistry, QD241-441, Bacillus subtilis., benzimidazoles, Article

Tidwell R. R.; Boykin D. W. Dicationic DNA Minor Groove Binders as Antimicrobial Agents, in Small Molecule DNA and RNA Binders: From Synthesis to Nucleic Acid Complexes; Demeunynck, M.; Bailly, C. and Wilson, W. D. (Eds.); Wiley-VCH: New York, 2003; Vol 2, pp 414-460.

E. Activity of dicationically substituted bis-benzimidazoles against experimental Pneumocystis carinii pneumonia. Antimicrob. Agents Chemother. 1993, 3, 1713-1716.

Hopkins, K.; Wilson, W. D.; Bender, B.; McCurdy, D.; Hall, J.E; Tidwell R. R.; Kumar, A.; Bajic, M.; Boykin, D.W. Extended Aromatic Furan Amidino Derivatives as Anti-Pneumocystis carinii Agents. J. Med. Chem. 1998, 41, 3872-3878.

Del Poeta M.; Schell, W. A.; Dykstra C. C.; Jones, S.; Tidwell, R. R.; Czarny, A.; Bajic, M.; Kumar, A.; Boykin, D. W.; Perfect, J. R. Structure-In Vitro Activity Relationships of Pentamidine Analogues and Dication-Substituted Bis-Benzimidazoles as New Antifungal Agents. Antimicrob. Agents Chemother. 1998, 42, 2495-2502. [OpenAIRE]

5. Del Poeta M.; Schell W.A.; Dykstra C.C.; Jones S.; Tidwell R.R.; Kumar, A.; Boykin, D.W.; Perfect, J.R. In Vitro Antifungal Activities of a Series of Dicationic-Substituted Carbazoles, Furans, and Benzimidazoles. Antimicrob. Agents Chemother. 1998, 42, 2503-2509. [OpenAIRE]

6. Ismail, M.A.; Brun, R;. Tanious, F .A.; Wilson, W. D.; Boykin, D. W. Synthesis and AntiProtozoal Activity of Aza-Analogs of Furamidine, J. Med. Chem. 2003, 46, 4761-4769.

7. Givens, M. D.; Dykstra, C. C.; Brock, K. V.; Stringfellow, D.A.; Kumar, A.; Stephens, C. E.; Goker, H.; Boykin, D. W. In Vitro Inhibition of Replication of Bovine Viral Diarrhea Virus by Aromatic Cationic Molecules, Antimicrob. Agents Chemother. 2003, 47, 2223- 2230. [OpenAIRE]

8. Bance, S,; Barber, H. J.; Woolman, A. M. Bromination of diphenylalkanes and the preparation of some stilbene derivatives. J. Chem. Soc. 1943, 1-4.

9. Dann, O.; Hieke, E.; Hahn, H.; Miserre, H.H.; Luerding, G.; Roessler, R. Polynuclear thiophenes VII. Trypanocidal diamidines of 2-phenylthionaphththene. Ann. Chem. 1970, 734, 23-45.

10. Fairly, T. A.; Tidwell, R. R.; Donkor, I.; Naiman, N.A.; Ohemeng, K. A.; Lombardy, R. J.; Bentley, J. Cory, M. Struture, DNA minor groove binding and base pair specificity of alkyl- and aryl linked bis(amidinobenzimidazoles) and bis(amidinoindoles) J. Med. Chem. 1993, 36, 1746- 1753.

11. Patrick, D. G.; Boykin, D. W.; Spychala, J.; Wilson, W. D.; Bender, B.K.; Hall, J. E.; Tidwell, R. R. Anti-pneumocystis carinii pneumonia activity of dicationic carazoles. Eur. J. Med. Chem. 1997, 32, 781-793.

12. Hamada, M. The preparation and properties of 1,2-diphenyl cyclopropanes. Ann. Chem. 1951, 22- 28.

13. Sambrook, J., Fritchsch, E.F., Maniatis, T. Molecular Cloning: A Laboratory Manual-2nd ed; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, N.Y., 1989.

Abstract
The synthesis of extended dicationic bis-benzimidazoles starting from trans‑1,2-bis(4-cyanophenyl)ethene and trans‑1,2-bis(4-cyanophenyl)cyclopropane is reported. The target diamidines show significant in vitro activity against B. subtilis.
Subjects
free text keywords: amidines, DIBAL reduction, Organic chemistry, QD241-441, Bacillus subtilis., benzimidazoles, Article

Tidwell R. R.; Boykin D. W. Dicationic DNA Minor Groove Binders as Antimicrobial Agents, in Small Molecule DNA and RNA Binders: From Synthesis to Nucleic Acid Complexes; Demeunynck, M.; Bailly, C. and Wilson, W. D. (Eds.); Wiley-VCH: New York, 2003; Vol 2, pp 414-460.

E. Activity of dicationically substituted bis-benzimidazoles against experimental Pneumocystis carinii pneumonia. Antimicrob. Agents Chemother. 1993, 3, 1713-1716.

Hopkins, K.; Wilson, W. D.; Bender, B.; McCurdy, D.; Hall, J.E; Tidwell R. R.; Kumar, A.; Bajic, M.; Boykin, D.W. Extended Aromatic Furan Amidino Derivatives as Anti-Pneumocystis carinii Agents. J. Med. Chem. 1998, 41, 3872-3878.

Del Poeta M.; Schell, W. A.; Dykstra C. C.; Jones, S.; Tidwell, R. R.; Czarny, A.; Bajic, M.; Kumar, A.; Boykin, D. W.; Perfect, J. R. Structure-In Vitro Activity Relationships of Pentamidine Analogues and Dication-Substituted Bis-Benzimidazoles as New Antifungal Agents. Antimicrob. Agents Chemother. 1998, 42, 2495-2502. [OpenAIRE]

5. Del Poeta M.; Schell W.A.; Dykstra C.C.; Jones S.; Tidwell R.R.; Kumar, A.; Boykin, D.W.; Perfect, J.R. In Vitro Antifungal Activities of a Series of Dicationic-Substituted Carbazoles, Furans, and Benzimidazoles. Antimicrob. Agents Chemother. 1998, 42, 2503-2509. [OpenAIRE]

6. Ismail, M.A.; Brun, R;. Tanious, F .A.; Wilson, W. D.; Boykin, D. W. Synthesis and AntiProtozoal Activity of Aza-Analogs of Furamidine, J. Med. Chem. 2003, 46, 4761-4769.

7. Givens, M. D.; Dykstra, C. C.; Brock, K. V.; Stringfellow, D.A.; Kumar, A.; Stephens, C. E.; Goker, H.; Boykin, D. W. In Vitro Inhibition of Replication of Bovine Viral Diarrhea Virus by Aromatic Cationic Molecules, Antimicrob. Agents Chemother. 2003, 47, 2223- 2230. [OpenAIRE]

8. Bance, S,; Barber, H. J.; Woolman, A. M. Bromination of diphenylalkanes and the preparation of some stilbene derivatives. J. Chem. Soc. 1943, 1-4.

9. Dann, O.; Hieke, E.; Hahn, H.; Miserre, H.H.; Luerding, G.; Roessler, R. Polynuclear thiophenes VII. Trypanocidal diamidines of 2-phenylthionaphththene. Ann. Chem. 1970, 734, 23-45.

10. Fairly, T. A.; Tidwell, R. R.; Donkor, I.; Naiman, N.A.; Ohemeng, K. A.; Lombardy, R. J.; Bentley, J. Cory, M. Struture, DNA minor groove binding and base pair specificity of alkyl- and aryl linked bis(amidinobenzimidazoles) and bis(amidinoindoles) J. Med. Chem. 1993, 36, 1746- 1753.

11. Patrick, D. G.; Boykin, D. W.; Spychala, J.; Wilson, W. D.; Bender, B.K.; Hall, J. E.; Tidwell, R. R. Anti-pneumocystis carinii pneumonia activity of dicationic carazoles. Eur. J. Med. Chem. 1997, 32, 781-793.

12. Hamada, M. The preparation and properties of 1,2-diphenyl cyclopropanes. Ann. Chem. 1951, 22- 28.

13. Sambrook, J., Fritchsch, E.F., Maniatis, T. Molecular Cloning: A Laboratory Manual-2nd ed; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, N.Y., 1989.

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publication . Other literature type . Article . 2004

The Synthesis of Dicationic Extended Bis-Benzimidazoles

Kang, Zhijan; Dykstra, Christine C.; Boykin, David W;