2,4-Diphenyl Furan Diamidines as Novel Anti-Pneumocystis carinii Pneumonia Agents
Dicationic 2,4-bis(4-amidinophenyl)furans 5−10 and 2,4-bis(4-amidinophenyl)-3,5-dimethylfurans 14 and 15 have been synthesized. Thermal melting studies revealed high binding affinity of the compounds to poly(dA-dT) and to the duplex oligomer d(CGCGAATTCGCG)2. All of the new compounds were effective...
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Published in | Journal of medicinal chemistry Vol. 42; no. 12; pp. 2260 - 2265 |
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Main Authors | , , , , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
17.06.1999
Amer Chemical Soc |
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Abstract | Dicationic 2,4-bis(4-amidinophenyl)furans 5−10 and 2,4-bis(4-amidinophenyl)-3,5-dimethylfurans 14 and 15 have been synthesized. Thermal melting studies revealed high binding affinity of the compounds to poly(dA-dT) and to the duplex oligomer d(CGCGAATTCGCG)2. All of the new compounds were effective against Pneumocystis carinii pneumonia in the immunosuppressed rat model with up to 200-fold increase in activity compared to the control compound pentamidine. No toxicity was noted for 5, 7−10 at the dose of 10 μmol/kg/d; however, the isopropyl analogue 7 showed toxicity comparable to pentamidine at the dosage of 20 μmol/kg/d. Dimethylation of the parent compound on the furan ring resulted in reduced activity and increased toxicity. |
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AbstractList | Dicationic 2,4-bis(4-amidinophenyl)furans 5-10 and 2,4-bis(4-amidinophenyl)-3,5-dimethylfurans 14 and 15 have been synthesized. Thermal melting studies revealed high binding affinity of the compounds to poly(dA-dT) and to the duplex oligomer d(CGCGAATTCGCG)(2). All of the new compounds were effective against Pneumocystis carinii pneumonia in the immunosuppressed rat model with up to 200-fold increase in activity compared to the control compound pentamidine. No toxicity was noted for 5, 7-10 at the dose of 10 mu mol/kg/d; however, the isopropyl analogue 7 showed toxicity comparable to pentamidine at the dosage of 20 mu mol/kg/d. Dimethylation of the parent compound on the furan ring resulted in reduced activity and increased toxicity. Dicationic 2,4-bis(4-amidinophenyl)furans 5-10 and 2, 4-bis(4-amidinophenyl)-3,5-dimethylfurans 14 and 15 have been synthesized. Thermal melting studies revealed high binding affinity of the compounds to poly(dA-dT) and to the duplex oligomer d(CGCGAATTCGCG)2. All of the new compounds were effective against Pneumocystis carinii pneumonia in the immunosuppressed rat model with up to 200-fold increase in activity compared to the control compound pentamidine. No toxicity was noted for 5, 7-10 at the dose of 10 micromol/kg/d; however, the isopropyl analogue 7 showed toxicity comparable to pentamidine at the dosage of 20 micromol/kg/d. Dimethylation of the parent compound on the furan ring resulted in reduced activity and increased toxicity. Dicationic 2,4-bis(4-amidinophenyl)furans 5−10 and 2,4-bis(4-amidinophenyl)-3,5-dimethylfurans 14 and 15 have been synthesized. Thermal melting studies revealed high binding affinity of the compounds to poly(dA-dT) and to the duplex oligomer d(CGCGAATTCGCG)2. All of the new compounds were effective against Pneumocystis carinii pneumonia in the immunosuppressed rat model with up to 200-fold increase in activity compared to the control compound pentamidine. No toxicity was noted for 5, 7−10 at the dose of 10 μmol/kg/d; however, the isopropyl analogue 7 showed toxicity comparable to pentamidine at the dosage of 20 μmol/kg/d. Dimethylation of the parent compound on the furan ring resulted in reduced activity and increased toxicity. |
Author | Tanious, Farial A Hall, James E Bender, Brendan C Francesconi, Iris Wilson, W. David Tidwell, Richard R McCurdy, Donald Boykin, David W |
Author_xml | – sequence: 1 givenname: Iris surname: Francesconi fullname: Francesconi, Iris – sequence: 2 givenname: W. David surname: Wilson fullname: Wilson, W. David – sequence: 3 givenname: Farial A surname: Tanious fullname: Tanious, Farial A – sequence: 4 givenname: James E surname: Hall fullname: Hall, James E – sequence: 5 givenname: Brendan C surname: Bender fullname: Bender, Brendan C – sequence: 6 givenname: Richard R surname: Tidwell fullname: Tidwell, Richard R – sequence: 7 givenname: Donald surname: McCurdy fullname: McCurdy, Donald – sequence: 8 givenname: David W surname: Boykin fullname: Boykin, David W |
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Keywords | PENTAMIDINE ANALOGS Pneumonia Intravenous administration Rat Furan derivatives Pneumocystis carinii Oxygen heterocycle Fungi Antifungal agent Structure activity relation Hydrochlorides Fungi Imperfecti Chemical synthesis Thallophyta Lung disease Opportunistic infection Minor groove Respiratory disease Rodentia Vertebrata Amidine Chemotherapy Biological fixation Experimental disease Mammalia Treatment Animal DNA Benzenic compound |
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Snippet | Dicationic 2,4-bis(4-amidinophenyl)furans 5−10 and 2,4-bis(4-amidinophenyl)-3,5-dimethylfurans 14 and 15 have been synthesized. Thermal melting studies... Dicationic 2,4-bis(4-amidinophenyl)furans 5-10 and 2,4-bis(4-amidinophenyl)-3,5-dimethylfurans 14 and 15 have been synthesized. Thermal melting studies... Dicationic 2,4-bis(4-amidinophenyl)furans 5-10 and 2, 4-bis(4-amidinophenyl)-3,5-dimethylfurans 14 and 15 have been synthesized. Thermal melting studies... |
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SubjectTerms | Amidines - chemical synthesis Amidines - chemistry Amidines - pharmacology Amidines - toxicity Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antifungal agents Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology Antifungal Agents - toxicity Biological and medical sciences Chemistry, Medicinal DNA - chemistry Furans - chemical synthesis Furans - chemistry Furans - pharmacology Furans - toxicity Immunocompromised Host Life Sciences & Biomedicine Medical sciences Pharmacology & Pharmacy Pharmacology. Drug treatments Pneumonia, Pneumocystis - drug therapy Rats Science & Technology Structure-Activity Relationship |
Title | 2,4-Diphenyl Furan Diamidines as Novel Anti-Pneumocystis carinii Pneumonia Agents |
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