(Vinylaryloxy)acetic acids. A new class of diuretic agents. 3. [(2-Nitro-1-alkenyl)aryloxy]acetic acids

Abstract

A series of [(2-nitro-1-alkenyl)aryloxy]acetic acids was synthesized and tested in dogs for saluretic and diuretic activity. A number of these compounds exhibit a high order of activity on iv or po administration; representative of these is (E)-[2,3-dichloro-4-(2-nitropropenyl)phenoxy]acetic acid (5). The most highly active compounds are qualitatively similar in action to [2,3-dichloro-4-(2-methylenebutyryl)phenoxylacetic acid (ethacrynic acid) in causing a prompt increase in the excretion of water and of sodium and chloride ions in approximately equimolar amounts but are three to five times as potent. Potassium ion excretion is increased but less markedly than sodium excretion.

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

“…The reaction of the o -nitrotoluene 51 with N,N- dimethylformamide dimethyl acetal in DMF gave the enamine 52 , which underwent oxidative cleavage using sodium periodate in THF to give aldehyde 62b via a more facile preparation than previously reported . A more expedient synthesis of aldehyde 62c is also reported. Commercially available chlorotoluene 53 underwent α-bromination to 54 by a modification of the original procedure.…”

“…The residue was partitioned between water and EtOAc to give white solid (8.63 g, 89%). An analytical sample was recrystallized from aqueous EtOH to give white needles: mp 117−119 °C (lit . 122−123°); 1 H NMR δ 10.34 (s, 1 H), 8.29 (m, 1H), 8.00 (m, 2H).…”

“…An analytical sample was recrystallized from aqueous EtOH to give white needles: mp 117-119 °C (lit. 39 General Procedure for Benzaldehyde Chlorooximes 64. N-Chlorosuccinimide (1.1 equiv) was added to a stirred solution of an aldoxime 63 in DMF at 0 °C.…”

A molecular electron density theory study of the Lewis acid–catalyzed decomposition reaction of nitroethyl benzoate using aluminum derivatives

“…Conjugated nitroalkenes (CNA) constitute an important class of organic compounds that have been extensively studied due to their biological activity . The pesticidal, fungicidal, and molluscicidal activities of many aromatic and heteroaromatic nitroalkenes have been reported, along with their ability to behave as diuretic agents and other bioactive materials . Furthermore, nitroalkenes are useful intermediates in the synthesis of many pharmaceutically interesting compounds and drugs, for example, antiulcer randitidine and nizatidine and other bioactive natural products …”

Synthesis and evaluation of α-hydroxymethylated conjugated nitroalkenes for their anticancer activity: Inhibition of cell proliferation by targeting microtubules

“…Nitro compounds, particularly conjugated nitroalkenes, also constitute an important class of compounds that has been extensively studied for its biological activity. 3 The pesticidal, Besides their own ability to behave as phosphate ester mimics, 7 diuretic agents 8 and other bioactive materials, 9 nitroalkenes are useful intermediates in the synthesis of drugs, e.g. antiulcer ranitidine and nizatidine, 10 and other bioactive natural products.…”