The Action of Phosphorus Pentahalides and Thionyl Chloride on Some Saturated and Unsaturated 1,4-Diketones and 2,5-Diphenylfurans

Lutz, Robert E.; Wilder, Frank N.

doi:10.1021/ja01325a049

Cited by 2 publications

(3 citation statements)

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“…This generalization especially applies to the quaternary cyclic amidines (8-11) which show very limited activity and are quite toxic. Most of the 2.5-bis(4-guanylphenyl)furans (4,17,25,32,38) show somewhat superior activity to stilbamidine, hydroxystilbamidine, and pentamidine in this test. Unfortunately, test results at lower dosage levels for stilbamidine and hydroxystilbamidine are not available for further comparison.…”

Section: Scheme IV 36 37mentioning

confidence: 89%

“…Unfortunately, test results at lower dosage levels for stilbamidine and hydroxystilbamidine are not available for further comparison. The substitution of one methyl group on the furan ring (25) produces a slight enhancement of activity, whereas two methyl groups (17) do not cause much change in biological response in comparison to the parent compound 4. Similarly, introduction of one chlorine (32) on the furan ring appears to slightly enhance activity, whereas two chlorine atoms (31) reduce the activity in comparison to 4.…”

Section: Scheme IV 36 37mentioning

confidence: 99%

“…Rl = "<0 CN Scheme III (Scheme I). 2,5-Bis(4-bromophenyl)furan (2) was also used as an intermediate for the preparation of the 3,4dimethyl-2,5-bis(4-guanylphenyl)furan analogues [17][18][19][20] and is patterned after a reported method of preparation of 2,5-diphenyl-3,4-dimethylfuran14 (Scheme II). It has been reported that 2,5-bis(p-bromophenyl)-3bromo-4-bromomethylfuran could be converted into 2.5-bis(p-bromophenyl)-3-methylfuran by a two-step process.…”

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Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)furans

Das¹,

Boykin²

1977

J. Med. Chem.

150

196

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Eighteen substituted 2,5-bis(4-guanylphenyl)furans and related analogues, including "masked" amidines in which the guanyl function is incorporated into a heterocyclic ring, have been synthesized and their antimalarial and antitrypanosomal activity has been evaluated. None of the compounds exhibited high orders of antimalarial activity; however, 11 were very active against Trypanosoma rhodesiense in mice. Six compounds, including 2,5-bis(4-guanylphenyl)furan (4) and its 3-chloro (32), 3,4-dichloro (31), 3-methyl (25), 3,4-dimethyl (20), and 3-chloro-4-methyl (38) derivatives, produced cures in mice at submilligram dosage levels; the 3,4-dimethyl (20) analogue exhibited a prolonged curative effect providing protection for 30 days after a single dose against a challenge by T. rhodesiense. These six compounds are somewhat more active in this screen than stilbamidine, hydroxystilbamidine, and pentamidine. The "masked" amidines generally exhibited lower antitrypanosomal activity than their true guanyl counterparts. Compound 4 was synthesized from 1,4-di-p-bromophenyl-1,4-butanedione by cyclodehydrative furanization to 2,5-bis(4-bromophenyl)furan (2) which was allowed to react with Cu2(CN)2 to produce the corresponding bis-nitrile 3. The latter compound was ultimately converted by way of an imidate ester into 4. Similarly, the 3- and/or 4-substituted derivatives of 2 were employed to prepare the other members of the series.

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Section: Scheme IV 36 37mentioning

confidence: 89%

Section: Scheme IV 36 37mentioning

confidence: 99%

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