425674-89-1

Upstream product

• 50704-52-4 methyl 3-(3-methoxyphenyl)propionate 
• 10516-71-9 3-(3-Methoxy-phenyl)-propionic acid 
• 7116-39-4 3-(3-methoxyphenyl)propanoic acid ethyl ester 

Downstream Products

• 1403568-99-9 C₁₇H₁₆ClN₃OS 
• 1067204-31-2 4-(4-chlorophenyl)-1-(3-(3-methoxyphenyl)propanoyl)thiosemicarbazide 
• 1403569-01-6 C₁₈H₁₉N₃O₂S 
• 1403568-85-3 4-(4-methoxyphenyl)-1-(3-(3-methoxyphenyl)propanoyl)thiosemicarbazide 
• 1403569-08-3 C₁₈H₁₉N₃O₂S 
• 1403568-91-1 4-(2-methoxyphenyl)-1-(3-(3-methoxyphenyl)propanoyl)thiosemicarbazide 
• 1215204-71-9 N-(2-methoxyphenyl)-2-(3-(3-methoxyphenyl)propanoyl)hydrazinecarboxamide 
• 1215204-70-8 3-(3-methoxyphenethyl)-4-(2-methoxyphenyl)-1H-1,2,4-triazol-5(4H)-one 
• 1353757-04-6 N-(3-methoxyphenyl)-2-(3-(3-methoxyphenyl)propanoyl)hydrazinecarboxamide 
• 1353757-12-6 3-(3-methoxyphenethyl)-4-(3-methoxyphenyl)-1H-1,2,4-triazol-5(4H)-one 
• 1353757-05-7 N-(4-methoxyphenyl)-2-(3-(3-methoxyphenyl)propanoyl)hydrazinecarboxamide 

Relevant academic research and scientific papers

Structure activity relationship of brevenal hydrazide derivatives

Brevenal is a ladder frame polyether produced by the dinoflagellate Karenia brevis. This organism is also responsible for the production of the neurotoxic compounds known as brevetoxins. Ingestion or inhalation of the brevetoxins leads to adverse effects such as gastrointestinal maladies and bronchoconstriction. Brevenal shows antagonistic behavior to the brevetoxins and shows beneficial attributes when administered alone. For example, in an asthmatic sheep model, brevenal has been shown to increase tracheal mucosal velocity, an attribute which has led to its development as a potential treatment for Cystic Fibrosis. The mechanism of action of brevenal is poorly understood and the exact binding site has not been elucidated. In an attempt to further understand the mechanism of action of brevenal and potentially develop a second generation drug candidate, a series of brevenal derivatives were prepared through modification of the aldehyde moiety. These derivatives include aliphatic, aromatic and heteroaromatic hydrazide derivatives. The brevenal derivatives were tested using in vitro synaptosome binding assays to determine the ability of the compounds to displace brevetoxin and brevenal from their native receptors. A sheep inhalation model was used to determine if instillation of the brevenal derivatives resulted in bronchoconstriction. Only small modifications were tolerated, with larger moieties leading to loss of affinity for the brevenal receptor and bronchoconstriction in the sheep model.

Synthesis, crystal structure and b-glucuronidase inhibition activity of some new hydrazinecarboxamides and their 1,2,4-triazole derivatives

A new series of hydrazinecarboxamides (5a-n), bearing various methoxyphenyl and methoxyphenethyl groups, was synthesized by condensation of corresponding acid hydrazides (3a-f) with methoxyphenylisocyanates (4a-c). Dehydrocyclization of hydrazinecarboxamides (5a-n) yielded corresponding methoxyphenyl and methoxyphenethyl substituted triazoles (6a-l) by refluxing in 2 N aqueous sodium hydroxide solution. All the synthesized compounds were screened for their b-glucuronidase inhibition activity. Compounds 5a, 5e, 5h, and 5l exhibited an excellent b-glucuronidase inhibitory activity as compared to the standard inhibitor. Springer Science+Business Media, LLC 2011.

Synthesis, urease and acetylcholine esterase inhibition activities of some 1,4-disubstituted thiosemicarbazides and their 2,5-disubstituted thiadiazoles

A new series of 2,5-disubstituted-1,3,4-thiadiazoles 6a-i was synthesized by overnight stirring various 1,4-disubstituted thiosemicarbazides 5a-i in polyphosphoric acid followed by neutralization. The structures of newly synthesized compounds 5a-i and 6a-i were characterized by IR, 1H and 13C NMR, elemental analysis and mass spectrometric studies. All the synthesized compounds were evaluated for their urease and acetylcholine esterase inhibition activities. Thiosemicarbazides 5a-i are found to possess excellent potential for urease inhibition, more than the standard drug. Thiosemicarbazides 5a-i are more potent urease inhibitor than their cyclic analogues thiadiazoles 6a-i. Almost all of the compounds are excellent inhibitors of acetylcholine esterase. The inhibition of acetylcholine esterase of compounds 5a, 5c, 5d, 5g, 5i, 6e, 6f, 6g, and 6i is much more than that of standard drug.

Synthesis, acetylcholinesterase and alkaline phosphatase inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives

A new series of 4,5-disubstituted-2,4-dihydro-3H-1,2,4-triazole-3-thiones (6as) and 2,5-disubstituted-1,3,4-thiadiazoles (7ah) was synthesized by intramolecular dehydrocyclization of various 1,4-disubstituted thiosemicarbazide derivatives (5as) by refluxing in 4N aqueous sodium hydroxide and by overnight stirring with polyphosphoric acid, respectively. The structures of these compounds were characterized by IR, 1H and 13C NMR, elemental analysis and mass spectroscopic studies. All the synthesized compounds were screened for their acetylcholinesterase and alkaline phosphatase inhibition studies. Most of the tested compounds showed promising activities, amongst them (6k) and (6q) showed excellent acetylcholinesterase inhibitory activity with IC50 0.2410.012 and 0.2600.013M, respectively, as compared with those of standard drug whereas the compound (6p), with IC50 0.0440.001M, was found to be the most potent inhibitor of alkaline phosphatase.

Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles

Appropriate aryl-substituted unsymmetrical azodicarbonyl compounds, generated from bishydrazides by oxidation, undergo intramolecular cyclisations to furnish a variety of useful heterocycles such as N-substituted oxindoles, carbostyrils, benzazepinones, benzazocinones, benzimidazolones, benzoxazinones and pyrazolones in varying degrees of efficiency. Methods are described to remove the N-acyl groups from the heteroaromatic compounds. Under mildly acidic conditions where equal opportunities are available for an ipso or a normal cyclisation it is the former process that occurs preferentially. Evidence is presented in favour of a C-to-C migration in the ipso product for the formation of a methoxy-substituted carbostyril derivative. One of the spiro substances is shown to participate in dienone-phenol rearrangement to provide the corresponding quinolone-phenol in high yield.