Synthesis of 2,3,5-trihydroxyphenylprop-1-ene and its 4-chloro-, 6-chloro-, and 4,6-dichloro- derivatives

Hill, Robert A.; Macaulay, G. S.; MacLachlan, William S.

doi:10.1039/p19870002209

Cited by 6 publications

(2 citation statements)

References 3 publications

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“…36 R-Bromination of 55 using 1 equiv of N-bromosuccinimide gave little selectivity between the mono-and dibromo adducts, but the analogous reaction using 2.5 equiv gave dibromide 56 almost exclusively. Silver nitrate oxidation 43 of dibromide 56 gave aldehyde 44f. Commercially available carboxylic acid 57 and analogue 59 44 (prepared via a Sandmeyer reaction from commercially available 58) were converted to methyl esters 60 and 61, respectively.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles

et al. 2007

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3,5-bis(4-amidinophenyl)isoxazole (3)-an analogue of 2,5-bis(4-amidinophenyl)furan (furamidine) in which the central furan ring is replaced by isoxazole-and 42 novel analogues were prepared by two general synthetic pathways. The 43 isoxazole derivatives were assayed against Trypanosoma brucei rhodesiense (T. brucei rhodesiense) STIB900, Plasmodium falciparum (P. falciparum) K1, and rat myoblast L6 cells (for cytotoxicity) in vitro. Eleven compounds (3, 13, 16-18, 22, 26, 29, 31, 37, and 41) exhibited antitrypanosomal IC50 values less than 10 nM, five of which displayed cytotoxic indices (ratios of cytotoxic IC50 to antiprotozoal IC50 values) at least 10 times higher than that of furamidine. Eighteen compounds (4-8, 12, 14, 18-22, 25, 26, 28, 29, 32, and 43) were more active against P. falciparum than furamidine, with IC50 values less than 15 nM. Fourteen of these compounds had cytotoxic indices ranging between 10 and 120 times higher than that of furamidine, and five analogues exhibited high selectivity for P. falciparum over T. brucei rhodesiense.

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Section: Introductionmentioning

confidence: 99%

Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles

et al. 2007

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“…9 The bromination of (3-or 4-methylphenyl)acetate 24 or 25 using N-bromosuccinimide gave bromo-(3-or 4-dibromomethylphenyl)acetate 26 or 27, of which dibromomethyl group was oxidized to aldehyde 28 or 29 with silver nitrate (Scheme 3). 11 The reaction of salicylaldehyde 23a and 2-bromophenylacetates (28, 29) with K 2 CO 3 in DMF at 120 o C, afforded the 2-phenylbenzofuran compounds (30, 31) via a sequence of reactions including O-alkylation, ring closure and decarboxylation to form a benzofuran ring. The aldehyde group of 30 or 31 was further diversified to the various amines 34-39 by reductive amination.…”

Section: Introductionmentioning

confidence: 99%

Studies on Benzofuran-7-carboxamides as Poly(ADP-ribose) Polymerase-1 (PARP-1) Inhibitors

Lee¹,

Yi²,

Lee³

et al. 2012

Bulletin of the Korean Chemical Society

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Benzofuran-7-carboxamide was identified as a novel scaffold of poly(ADP-ribose) polymerase-1 (PARP-1) inhibitor. A series of compounds with various 2-substituents including (tertiary amino)methyl moieties substituted with aryl ring and aryl groups containing tertiary amines, were synthesized and biologically evaluated to elucidate the structure-activity relationships and optimize the potency. 2-[4-(Pyrrolidin-1-ylmethyl)phenyl]-benzofuran-7-carboxamide (42) was the most potent as an IC 50 value of 40 nM among those.

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ChemInform Abstract: Synthesis of 2,3,5‐Trihydroxyphenylprop‐1‐ene and Its 4‐Chloro, 6‐Chloro, and 4,6‐Dichloro Derivatives.

1988

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Synthesis of 2,3,5-trihydroxyphenylprop-1-ene and its 4-chloro-, 6-chloro-, and 4,6-dichloro- derivatives

Cited by 6 publications

References 3 publications

Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles

Synthesis and in Vitro Antiprotozoal Activities of Dicationic 3,5-Diphenylisoxazoles

Studies on Benzofuran-7-carboxamides as Poly(ADP-ribose) Polymerase-1 (PARP-1) Inhibitors

ChemInform Abstract: Synthesis of 2,3,5‐Trihydroxyphenylprop‐1‐ene and Its 4‐Chloro, 6‐Chloro, and 4,6‐Dichloro Derivatives.

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