119520-57-9Relevant academic research and scientific papers
Synthesis of Acetaminophen Analogues Containing α-Amino Acids and Fatty Acids for Inhibiting Hepatotoxicity
Imai, Nobuyuki,Jung, Seunghee,Kawashima, Yuya,Noguchi, Takuya
, p. 3686 - 3696 (2019/09/30)
Acetaminophen is a popular antipyretic analgesic medicine that has weaker anti-inflammatory properties and lower incidence of side effects than nonsteroidal anti-inflammatory drugs (NSAIDs). However, acetaminophen causes hepatotoxicity due to the reactive metabolite N -acetyl- p -benzoquinone imine (NAPQI). We have obtained acetaminophen analogues in 57-99percent yields by using aniline derivatives with protected α-amino acids and fatty acids via the corresponding mixed carbonic carboxylic anhydrides in aqueous MeCN. We have also succeeded in synthesizing AM404 analogues in 76-97percent yields, which are expected to be promising candidates for reducing hepatotoxicity.
Base-catalyzed synthesis of aryl amides from aryl azides and aldehydes
Xie, Sheng,Zhang, Yang,Ramstr?m, Olof,Yan, Mingdi
, p. 713 - 718 (2015/12/30)
Aryl amides have been used as important compounds in pharmaceuticals, materials and in molecular catalysis. The methods reported to prepare aryl amides generally require very specific reagents, and the most popular carboxyl-amine coupling reactions demand stoichiometric activators. Herein, we report that aryl azides react with aldehydes under base-catalyzed conditions to yield aryl amides efficiently. Mechanistic investigations support the formation of triazoline intermediates via azide-enolate cycloaddition, which subsequently undergo rearrangement to give amides by either thermal decomposition (20-140 °C) or aqueous acid work-up at room temperature. The strategy does not require nucleophilic anilines and is especially efficient for highly electron-deficient aryl amides, including perfluoroaryl amides, which are otherwise challenging to synthesize.
Convenient synthesis of acetaminophen analogues containing α-amino acids and fatty acids via their mixed carbonic carboxylic anhydrides in aqueous organic solvent
Jung, Seunghee,Tsukuda, Yuki,Kawashima, Rie,Ishiki, Takumi,Matsumoto, Ayaka,Nakaniwa, Aya,Takagi, Miho,Noguchi, Takuya,Imai, Nobuyuki
, p. 5718 - 5720 (2013/09/24)
Acetaminophen analogues containing α-amino acid and fatty acids were easily synthesized in 77-99% yields from the corresponding mixed carbonic carboxylic anhydrides of α-amino acid and fatty acids using aniline derivatives in aqueous MeCN.
QUINOLINE, NAPHTHALENE AND CONFORMATIONALLY CONSTRAINED QUINOLINE OR NAPHTHALENE DERIVATES AS ANTI-MYCOBACTERIAL AGENTS
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Page/Page column 24-25, (2009/08/16)
The invention relates to a compound of general formula I, II, III, IV V VI, VII, VIII, IX, X or a tautomer and the stereochemically isomeric forms thereof or pharmaceutically acceptable salts thereof, a N-oxide form thereof or a pro-drug thereof. The compound is usable as a medicament for the treatment of mycobacterial disease
Design, synthesis and biological evaluation of novel triazole, urea and thiourea derivatives of quinoline against Mycobacterium tuberculosis
Upadhayaya, Ram Shankar,Kulkarni, Girish M.,Vasireddy, Nageswara Rao,Vandavasi, Jaya Kishore,Dixit, Shailesh S.,Sharma, Vivek,Chattopadhyaya, Jyoti
experimental part, p. 4681 - 4692 (2009/12/04)
A new series of 20 quinoline derivatives possessing triazolo, ureido and thioureido substituents have been synthesized and their antimycobacterial properties have been evaluated. Compounds 10, 22 and 24 inhibited Mycobacterium tuberculosis H37Rv up to 96%, 98% and 94% respectively, at a fixed concentration of 6.25 μg/mL. Minimum inhibitory concentration of 3.125 μg/mL was obtained for compound 10 and 24, while for compound 22 it was 6.25 μg/mL. Molecular docking calculations suggest critical hydrogen bonding and electrostatic interactions between polar functional groups (such as quinoline-nitrogen, urea-carbonyl and hydroxyl) of anti-mycobacterial (anti-TB) compounds and amino acids (Arg186 and Glu61) of ATP-synthase of M. tuberculosis, could be the probable reason for observed anti-mycobacterial action.
Mild, powerful, and robust methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively
Nakatsuji, Hidefumi,Morimoto, Mami,Misaki, Tomonori,Tanabe, Yoo
, p. 12071 - 12080 (2008/03/13)
We developed two efficient practical methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively. The present mild and robust reaction was performed by two separate methods both by combining cheap and readily available amines, N-methylimidazole, and N,N,N′,N′-tetramethylethylenediamine (TMEDA). Method A uses catalytic N-methylimidazole and TMEDA with an equimolar amount of K2CO3, whereas Method B uses equimolar amounts of N-methylimidazole and TMEDA. The salient features are as follows. (i) With regard to reactivity, Method B was superior to Method A for esterification and thioesterification, whereas cost-effective Method A was superior to Method B for amide formation. (ii) Amide formation proceeded smoothly between acid chlorides and less nucleophilic and stereocongested amines such as 2,6-dichloroaniline. (iii) This protocol was applied to the successful synthesis of two agrochemicals, bromobutide and carpropamid.
THE INVENTION OF RADICAL REACTIONS PART XVIII. A CONVENIENT SOLUTION TO THE 1-CARBON PROBLEM (R-CO2H --> R-13CO2H)
Barton, Derek H. R.,Ozbalik, Nubar,Vacher, Bernard
, p. 3501 - 3512 (2007/10/02)
Radicals generated by photolysis (W light) of esters derived from N-hydroxy-2-thiopyridone react with electrophilic isocyanides 2a and (in the presence of trifluoroacetic acid) 2b to give adducts of type 3.Convenient reaction procedures have been worked out to hydrolyse the adducts to amides of type 5, from which the original acid can be regenerated under mild conditions.The three important acids oleic, linoleic and arachidonic have all given smooth reactions.In suitable examples, quantitative evolution of carbon dioxide and incorporation of 13C without dilution have been demonstrated.This reaction sequence will be useful for the labelling in the carboxyl group of prostaglandins, leukotrienes, and the side chain carboxyls of peptides.
