2,5- and 5,6-Dihalonicotinic acids and their precursors

Setliff, Frank L.

doi:10.1021/je60047a005

Cited by 13 publications

(9 citation statements)

References 2 publications

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“…2-Bromo-5-iodonicotinic acid 2n was synthesized by treatment of 2,5-dibromo-3-picoline 1n with i- propylmagnesium chloride in the presence of I 2 in tetrahydrofuran (THF) at room temperature for 24 h, followed by oxidation34 using KMnO 4 in water for 48 h at reflux temperature (Scheme 3). …”

Section: Chemistrymentioning

confidence: 99%

Design, Synthesis, and Structure−Activity Relationship of a Novel Series of 2-Aryl 5-(4-Oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans as HIV-1 Entry Inhibitors

et al. 2009

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We previously identified two small molecules targeting the HIV-1 gp41, N-(4-carboxy-3-hydroxy) phenyl-2,5-dimethylpyrrole 12 (NB-2) and N-(3-carboxy-4-chloro) phenylpyrrole 13 (NB-64) that inhibit HIV-1 infection at low μM level. Based on molecular docking analysis, we designed a series of 2-aryl 5-(4-oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans. Compared with 12 and 13, these compounds have bigger molecular size (437-515 Da) and could occupy more space in the deep hydrophobic pocket on the gp41 NHR-trimer. Fifteen 2-aryl 5-(4-oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans (11a-o) were synthesized by Suzuki-Miyaura cross coupling, followed by a Knoevenagel condensation and tested for their anti-HIV-1activity and cytotoxicity on MT-2 cells. We found that all 15 compounds had improved anti-HIV-1 activity and 3 of them (11a, 11b, and 11d) exhibited inhibitory activity against replication of HIV-1 IIIB and 94UG103 at <100 nM range, more than 20-fold more potent than 12 and 13, suggesting that these compounds can serve as leads for development of novel small molecule HIV fusion inhibitors.

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Section: Chemistrymentioning

confidence: 99%

Design, Synthesis, and Structure−Activity Relationship of a Novel Series of 2-Aryl 5-(4-Oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans as HIV-1 Entry Inhibitors

et al. 2009

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“…These dihalo acids were prepared by the oxidation of the appropriate dihalopicoline (II, III, Vil, and VIII, respectively) using potassium permanganate. The standard general procedure employed has been described previously (5,6).…”

Section: Methodsmentioning

confidence: 99%

“…Compounds possessing hypolipidemic activity are the subject of extensive pharmaceutical research. Halo and dihalonicotinic acids and their derivatives have received attention as potential hypolipidemic agents (1-4), and in this communication we wish to report the preparation and characterization of four new dihalonicotinic acids as an extension of our previous work (5)(6)(7)(8).…”

Section: Literature Citedmentioning

confidence: 99%

Some 2,5- and 5,6-dihalonicotinic acids and their precursors. 5

Setliff¹,

Greene²

1978

J. Chem. Eng. Data

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“…These dihaloacids were prepared by oxidation of the appropriate dihalopicoline (II, III, Vil, and VIII, respectively) using potassium permanganate. The general procedure employed has been previously described (6)(7)(8).…”

mentioning

confidence: 99%

“…(Supplemental information on the preparation of compounds and methods of determining data has been filed with the ACS Microfilm Depository Service.) Table I lists the observed values of the amides, as well as a tabulation of values calculated from the observed values or, in the case of calculated molar refractivity, values obtained from the Lorenz-Lorentz equation using standard tables and methods (2,4,6).…”

mentioning

confidence: 99%

Some 2,5- and 5,6-dihalonicotinic acids and their precursors. IV

Setliff¹,

LANE²

1976

J. Chem. Eng. Data

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The preparation of 2,5-dichloro-, 2-chloro-5-iodo-, 5,6dichloro-, and 6-chloro-5-iodonicotinic acid by oxidation of the appropriate dihalopicoline is described. The syntheses of the dihalopicolines are also presented. The generation of 5-chloro-6-iodonicotinic acid by iodide displacement of 5,6-dichloronicotinic acid is described. Experimental and spectral data for all new compounds are reported.In recent years haloand dihalonicotinic acids and their derivatives have received attention as potential hypolipidemic agents (1-4). We have previously reported the synthesis of a variety of dihalonicotinic acids of potential medicinal interest (6-8). In this communication we report the synthesis of dihalonicotinic acids IV, V, IX, and X by permanganate oxidation of the corresponding dihalopicolines II, III, Vil, and VIII, respectively. Acid XI was generated by prolonged reflux of acid IX with sodium iodide in methyl ethyl ketone.2,5-Dichloro-3-picoline (II) and 2-chloro-5-lodo-3-picoline (III) were obtained via dlazotlzatlon of 5-amino-2-chloro-3picoline (I) (7). 5,6-Dichloro-3-picoline (VII) and 6-chloro-5iodo-3-picoline (VIII) were produced in analogous fashion from 5-amlno-6-chloro-3-picollne (VI) (9).

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2,5- and 5,6-Dihalonicotinic acids and their precursors

Abstract: 4-( 1 -Chloroethyl)phenyl-bis(trifluoromethyl)carbinol. A 115gram portion of I in 500 ml of CC14 was chlorinated with 23.5 grams of chlorine over 0.75 hour at 60°to 76°u sing a 100-W Hanovia mercury vapor lamp. The mixture was separated by distillation to give 61 grams (47.4%) of 4-(l-

Cited by 13 publications

References 2 publications

Design, Synthesis, and Structure−Activity Relationship of a Novel Series of 2-Aryl 5-(4-Oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans as HIV-1 Entry Inhibitors

Design, Synthesis, and Structure−Activity Relationship of a Novel Series of 2-Aryl 5-(4-Oxo-3-phenethyl-2-thioxothiazolidinylidenemethyl)furans as HIV-1 Entry Inhibitors

Some 2,5- and 5,6-dihalonicotinic acids and their precursors. 5

Some 2,5- and 5,6-dihalonicotinic acids and their precursors. IV

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