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66356-53-4Relevant academic research and scientific papers
Synthesis of ranitidine (Zantac) from cellulose-derived 5-(chloromethyl)furfural
Mascal, Mark,Dutta, Saikat
, p. 3101 - 3102 (2011)
The biomass-derived platform chemical 5-(chloromethyl)furfural is converted into the blockbuster antiulcer drug ranitidine (Zantac) in four steps with an overall 68% isolated yield. The Royal Society of Chemistry.
Synthesis and biological evaluation of ranitidine analogs as multiple-target-directed cognitive enhancers for the treatment of Alzheimer's disease
Gao, Jie,Midde, Narasimha,Zhu, Jun,Terry, Alvin V.,McInnes, Campbell,Chapman, James M.
, p. 5573 - 5579 (2016/11/09)
Using molecular modeling and rationally designed structural modifications, the multi-target structure–activity relationship for a series of ranitidine analogs has been investigated. Incorporation of a variety of isosteric groups indicated that appropriate aromatic moieties provide optimal interactions with the hydrophobic and π–π interactions with the peripheral anionic site of the AChE active site. The SAR of a series of cyclic imides demonstrated that AChE inhibition is increased by additional aromatic rings, where 1,8-naphthalimide derivatives were the most potent analogs and other key determinants were revealed. In addition to improving AChE activity and chemical stability, structural modifications allowed determination of binding affinities and selectivities for M1–M4 receptors and butyrylcholinesterase (BuChE). These results as a whole indicate that the 4-nitropyridazine moiety of the JWS-USC-75IX parent ranitidine compound (JWS) can be replaced with other chemotypes while retaining effective AChE inhibition. These studies allowed investigation into multitargeted binding to key receptors and warrant further investigation into 1,8-naphthalimide ranitidine derivatives for the treatment of Alzheimer's disease.
Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis
Galkin, Konstantin I.,Krivodaeva, Elena A.,Romashov, Leonid V.,Zalesskiy, Sergey S.,Kachala, Vadim V.,Burykina, Julia V.,Ananikov, Valentine P.
, p. 8338 - 8342 (2016/07/19)
Spectral studies revealed the presence of a specific arrangement of 5-hydroxymethylfurfural (5-HMF) molecules in solution as a result of a hydrogen–bonding network, and this arrangement readily facilitates the aging of 5-HMF. Deterioration of the quality of this platform chemical limits its practical applications, especially in synthesis/pharma areas. The model drug Ranitidine (Zantac) was synthesized with only 15 % yield starting from 5-HMF which was isolated and stored as an oil after a biomass conversion process. In contrast, a much higher yield of 65 % was obtained by using 5-HMF isolated in crystalline state from an optimized biomass conversion process. The molecular mechanisms responsible for 5-HMF decomposition in solution were established by NMR and ESI-MS studies. A highly selective synthesis of a 5-HMF derivative from glucose was achieved using a protecting group at O(6) position.
Synthesis of HIV-1 capsid protein assembly inhibitor (CAP-1) and its analogues based on a biomass approach
Romashov, Leonid V.,Ananikov, Valentine P.
, p. 10593 - 10598 (2016/11/30)
A biomass-derived platform chemical was utilized to access a demanded pharmaceutical substance with anti-HIV activity (HIV, human immunodeficiency virus) and a variety of structural analogues. Step economy in the synthesis of the drug core (single stage from cellulose) is studied including flexible variability of four structural units. The first synthesis and X-ray structure of the inhibitor of HIV-1 capsid protein assembly (CAP-1) is described.
Synthesis of highly fluorescent and water soluble perylene bisimide
Boobalan, Gopal,Imran, Predhanekar Mohamed,Nagarajan, Samuthira
, p. 149 - 153 (2012/06/29)
Designed and synthesized a new highly water soluble N,N′-bis(2-((5- ((dimethylamino)methyl)furan-2-yl)methylthio)ethyl)perylene-3,4,9, 10-tetracarboxylic diimide from 2-((5-((dimethylamino)methyl)furan-2-yl) methylthio)ethanamine and perylene-3,4,9,10-tetracarboxylic dianhydride. The compound was characterized by 1H, 13C, 2D NMR, mass and IR techniques. The compound is highly fluorescent with good solubility in water and other polar solvents.
Synthesis and pharmacology of two new histamine receptor antagonists related to ranitidine
Navarro,Almeida,Anaya,Moran,Grande,Caballero,Palacios,Montero,San Roman
, p. 12 - 15 (2007/10/02)
Pyridyl and 1,6-dihydropyridyl ranitidine analogues 1 and 2 were obtained by applying an improved modification of ranitidine synthesis. Compound 1 shows a selective H2 antagonistic activity while compound 2 is a non-selective histamine antagonist.
NOVEL INTERMEDIATES FOR RANITIDINE SYNTHESIS
Chachula, Stanislaw,Grynkiewicz, Grzegorz,Szczycinski, Bohdan
, p. 619 - 622 (2007/10/02)
New synthesis of ranitidine are described, in which the sulfide linkages have been generated through alkylation of S-alkylthiosulfates.
1,5-EPOXY-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINS AND USE IN TREATMENT OF ULCERS
-
, (2008/06/13)
The synthesis of epoxybenzazepin compounds is described. The novel compounds have anti-ulcer activity.
Isolation and Identification of the Hydrolytic Degradation Products of Ranitidine Hydrochloride
Haywood, Phillip A.,Martin-Smith, Michael,Cholerton, Trevor J.,Evans, Michael B.
, p. 951 - 954 (2007/10/02)
Hydrolytic degradative studies on ranitidine hydrochloride (1) have shown that two different pathways are operative under strongly acid and strongly alkaline conditions.At intermediate pH values both pathways are operative whilst at very low pH values ranitidine hydrochloride is resistant to hydrolytic cleavage.This resistance to hydrolysis may be ascribed to C- protonation of the enediamine.
FURAN DERIVATIVES HAVING ANTI-ULCER ACTIVITY
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, (2008/06/13)
Compounds of formula (I): STR1 wherein: A represents a CH-NO 2 group or a N-CN group;B represents CH 2, O, S or a direct bond;R represents a bicyclic or polycyclic residue, variously substituted and functionalized;R 1 and R 2, which may be the same or different, are hydrogen or C 1-C 4 alkyl groups; andn and m, which may be the same or different, are 0, 1, 2, 3 or 4; are valuable pharmacological agents.
