Substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazole-6-carboxylic acids: high-ceiling diuretics with uricosuric activity

Plattner, Jacob J.; Fung, Anthony K. L.; Parks, James A.; Pariza, R. J.; Crowley, Steven R.; Pernet, André G.; Bunnell, Paul R.; Dodge, Patrick W.

doi:10.1021/jm00374a014

Cited by 33 publications

(6 citation statements)

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“…Fortunately the products are easily separated so that using the latter amine we were able to obtain 9b (58%) and 10 (15%) on a gram scale. We observed a similar effect of amine bulk on the chlorination selectivity with phenol 11 , which gave a 0.8:1, 1.8:1, 2.4:1, or 2.6:1 mixture of 12 13 and 13 14 with sulfuryl chloride and t -butylamine, dipropylamine, diisopropylamine, or 2,2,6,6-tetramethylpiperidine, respectively.…”

supporting

confidence: 56%

Syntheses of Chloroisosulochrin and Isosulochrin and Biomimetic Elaboration to Maldoxin, Maldoxone, Dihydromaldoxin, and Dechlorodihydromaldoxin

Snider

2011

Org. Lett.

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An efficient synthesis of chloroisosulochrin was accomplished using a novel ortho-selective chlorination of a phenol with sulfuryl chloride and 2,2,6,6-tetramethylpiperidine as the key step. Further elaboration by a biomimetic route converted chloroisosulochrin to dihydromaldoxin, maldoxone (lactone formed by dehydration of dihydromaldoxin), and maldoxin and isosulochrin to dechlorodihydromaldoxin and dechloromaldoxin.

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supporting

confidence: 56%

Syntheses of Chloroisosulochrin and Isosulochrin and Biomimetic Elaboration to Maldoxin, Maldoxone, Dihydromaldoxin, and Dechlorodihydromaldoxin

Snider

2011

Org. Lett.

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“…The mixture was cooled to room temperature, and aqueous 1 N HCl (500 ml) was added to adjust the pH to 1. Extraction was performed with EtOAc (300 ml) twice, and the extracts were concentrated in vacuo to give product 7 (50 g, 85% yield); white powder36; mp 205–210 °C. 1 H-NMR(600 MHz, CD 3 OD) δ H 7.58(1H, d, J = 0.8 Hz, Ar-H), 7.41 (1H, t, J = 8.3 Hz, Ar-H), 7.16 (1H, d, J = 8.4 Hz, Ar-H), 6.79 (1H, d, J = 8.0 Hz, Ar-H), 3.96 (3H, s, OCH 3 ); 13 C-NMR(150 MHz, CD 3 OD) δ c 162.3, 158.2, 156.1, 146.0, 129.9, 119.0, 112.2, 105.6, 104.7, 56.2 (S13 and S14 Figs).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and anti-obesity effects in vivo of Crotadihydrofuran C as a novel PPARγ antagonist from Crotalaria albida

Sun

Zhang

Chou

2017

Sci Rep

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Crotadihydrofuran C (CC) from the herbs of Crotalaria albida is able to inhibit adipocyte differentiation and lipid accumulation. However, the effects of CC on obesity and metabolic disorders have not yet been elucidated. In our study, the first enantioselective synthesis of the 2-isopropenyl dihydrofuran isoflavone skeleton (CC) is described. The convenient and efficient synthetic protocols developed skilfully solve the problems of the ortho-para directing group and Suzuki coupling reaction using a boronic acid pinacol ester that was more stable and easy to obtain. Furthermore, CC treatment of high-fat diet (HFD)-fed obese mice remarkably reduced their body weight, fat mass, and lipid level as well as improved insulin resistance and non-alcoholic fatty liver disease (NAFLD). A TR-FRET assay showed that CC was specifically bound to PPARγ LBD, which was further confirmed by the molecular docking study. These results suggest that CC could be a useful and potential natural product for treating metabolic diseases, including obesity, hyperlipidemia insulin resistance and NAFLD, without toxic side-effects.

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“…Methyl 3-(3-chloro-2,4-dihydroxyphenyl) propanoate ( 4a ) ( Scheme 1 ) was synthesized starting from 3-chloro-2,4-dimethoxybenzaldehyde ( 1 ) ( 20 ), which was converted to substituted cinnamic acid 2 by Knoevenagel condensation. Intermediate 2 was hydrogenated in the presence of Pd/C to yield substituted phenyl propionic acid 3 , which was first demethylated with HBr/HOAc and then converted to the methyl ester 4a .…”

Section: Methodsmentioning

confidence: 99%

A novel endonuclease IV post-PCR genotyping system

Kutyavin¹,

Milesi²,

Belousov³

et al. 2006

Nucleic Acids Research

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Here we describe a novel endonuclease IV (Endo IV) based assay utilizing a substrate that mimics the abasic lesions that normally occur in double-stranded DNA. The three component substrate is characterized by single-stranded DNA target, an oligonucleotide probe, separated from a helper oligonucleotide by a one base gap. The oligonucleotide probe contains a non-fluorescent quencher at the 5′ end and fluorophore attached to the 3′ end through a special rigid linker. Fluorescence of the oligonucleotide probe is efficiently quenched by the interaction of terminal dye and quencher when not hybridized. Upon hybridization of the oligonucleotide probe and helper probe to their complementary target, the phosphodiester linkage between the rigid linker and the 3′ end of the probe is efficiently cleaved, generating a fluorescent signal. In this study, the use of the Endo IV assay as a post-PCR amplification detection system is demonstrated. High sensitivity and specificity are illustrated using single nucleotide polymorphism detection.

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Substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazole-6-carboxylic acids: high-ceiling diuretics with uricosuric activity

Cited by 33 publications

References 0 publications

Syntheses of Chloroisosulochrin and Isosulochrin and Biomimetic Elaboration to Maldoxin, Maldoxone, Dihydromaldoxin, and Dechlorodihydromaldoxin

Syntheses of Chloroisosulochrin and Isosulochrin and Biomimetic Elaboration to Maldoxin, Maldoxone, Dihydromaldoxin, and Dechlorodihydromaldoxin

Synthesis and anti-obesity effects in vivo of Crotadihydrofuran C as a novel PPARγ antagonist from Crotalaria albida

A novel endonuclease IV post-PCR genotyping system

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