Synthesis of C-heteryl-substituted aminomethylphosphonic acids derivatives

Golovchenko, A. V.; Solomyannyi, R. N.; Броварец, В. С.

doi:10.1134/s1070363210040067

Cited by 4 publications

(7 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…2 and 3, which without further purification were used for the preparation of pyrazole derivatives 4a-d,f and 5a,b,d-f. Some examples of such transformations of 4-oxo-4Hchromene-2-carboxamides to substituted pyrazoles were also described earlier [34]. The structure and composition of compounds 4a-d,f and 5a,b,d-f were confirmed by 1 H, 13 C NMR spectroscopy and elemental analysis.…”

Section: Chemistrymentioning

confidence: 66%

“…Starting 4-oxo-4H-chromene-2-carboxylic acids 1 [32,33] were initially converted into substituted amides 2 and 3, which without further purification were used for the preparation of pyrazole derivatives 4a-d,f and 5a,b,d-f. Some examples of such transformations of 4-oxo-4Hchromene-2-carboxamides to substituted pyrazoles were also described earlier [34].…”

Section: Chemistrymentioning

confidence: 86%

See 1 more Smart Citation

Carbonic Anhydrase Inhibition with Sulfonamides Incorporating Pyrazole- and Pyridazinecarboxamide Moieties Provides Examples of Isoform-Selective Inhibitors

Angeli

Карцев²,

Petrou

et al. 2021

Molecules

View full text Add to dashboard Cite

A series of benzenesulfonamides incorporating pyrazole- and pyridazinecarboxamides decorated with several bulky moieties has been obtained by original procedures. The new derivatives were investigated for the inhibition of four physiologically crucial human carbonic anhydrase (hCA, EC 4.2.2.1.1) isoforms, hCA I and II (cytosolic enzymes) as well as hCA IX and XII (transmembrane, tumor-associated isoforms). Examples of isoform-selective inhibitors were obtained for all four enzymes investigated here, and a computational approach was employed for explaining the observed selectivity, which may be useful in drug design approaches for obtaining inhibitors with pharmacological applications useful as antiglaucoma, diuretic, antitumor or anti-cerebral ischemia drugs.

show abstract

Section: Chemistrymentioning

confidence: 66%

Section: Chemistrymentioning

confidence: 86%

Carbonic Anhydrase Inhibition with Sulfonamides Incorporating Pyrazole- and Pyridazinecarboxamide Moieties Provides Examples of Isoform-Selective Inhibitors

Angeli

Карцев²,

Petrou

et al. 2021

Molecules

View full text Add to dashboard Cite

show abstract

“…Under the same conditions, not only recyclization, but also hydrolysis occurred with dialkyl phosphonates 46 (phosphorus analogues of compounds 44), and acids 47 were formed (Scheme 15b). [24] On the other hand, hydrolysis was easily avoided when recyclization of dialkyl phosphonates 46 took place in aqueous ethanol (Scheme 15c). [22,24,25] Remarkably, carboxylic acid esters 44 in aqueous ethanol proved stable.…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

“…[24] On the other hand, hydrolysis was easily avoided when recyclization of dialkyl phosphonates 46 took place in aqueous ethanol (Scheme 15c). [22,24,25] Remarkably, carboxylic acid esters 44 in aqueous ethanol proved stable.…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

Recyclization of 5‐Amino‐ oxazoles as a Route to new Functionalized Heterocycles (Developments of V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine)

Shablykin,

Brovarets,

Shablykina

2023

The Chemical Record

View full text Add to dashboard Cite

The recyclizations of 5‐amino‐ and 5‐hydrazine‐1,3‐oxazoles mainly with electron‐withdrawing group in 4th position are considered. The chemical behavior of these heterocycles is due to the presence of two hidden amide fragments; therefore, the recyclization processes include a stage of nucleophile attack on 2nd or 5th position of the oxazole cycle. When the nitrile group is present in 4th position, it is often involved in the recyclization forming α‐aminoazoles. 5‐Amino/hydrazine‐1,3‐oxazoles undergo recyclization both in nucleophilic (amines, hydrazine, thionating agents) and electrophilic medium ((trifluoro)acetic acid, other acylating agents). The numerous types of functionalized heterocycles can be easily obtained with the usage of these recyclizations, such as the derivatives of 3‐amino‐6,7‐dihydro‐5H‐pyrrolo[1,2–a]imidazole, imidazolidine‐2,4‐dione, 1H‐pyrazole‐3,4,5‐triamine, 5,6‐diamino‐2,3‐diphenylpyrimidin‐4(3H)‐one, 2‐(2‐R‐7‐oxo‐5‐(trifluoromethyl)oxazolo[5,4–d]pyrimidin‐6(7H)‐yl)acetic acid, 2‐R‐4‐(5‐R′‐1,3,4‐oxadiazol‐2‐yl)oxazol‐5‐amine, (amino(5‐amino‐1,3,4‐thiadiazol‐2‐yl)methyl)phosphonate.

show abstract

“…Рециклізація з одночасним розщепленням фосфоестерних зв'язків проходила при нагріванні в оцтовій кислоті з утворенням відповідних α-(1,3,4-оксадіазоліл)(аміно)метилфосфонових кислот 166. Варто зазначити, що отримані фосфонові кислоти 166 в оксадіазольному циклі містять додаткові гетероциклічні фрагменти фурану, тіофену, 5-феніл-1,2-оксазолу, кумарину, хромону та 6-метилхромону [57,69].…”

Section: гетероциклізації за участю α-та β-фосфоніленамінівunclassified

α(β)-Sulfonyl(phosphoryl)acrylonitriles and enamines in the synthesis of biologically active heterocycles

Solomyannyi¹,

Shablykina²,

Москвина³

et al. 2020

J. org. pharm. chem.

View full text Add to dashboard Cite

α(β)-Cульфоніл(фосфорил)акрилонітрили та енаміни в синтезі біоактивних гетероциклів Функціоналізація гетероциклічних систем фармакофорними сульфуро-та фосфоровмісними угрупуваннями давно зарекомендувала себе як ефективний метод створення нових лікарських засобів. Разом із тим, деякі з типів структур представлено лише поодинокими прикладами, що не дозволяє оцінити внесок певних структурних елементів у прояв біологічної дії досліджуваних сульфоніл-та фосфорилзаміщених гетероциклічних сполук. Тому розробка нових методів синтезу гетероциклічних сполук із сульфонільними та фосфорильними групами, а також встановлення біологічної активності таких продуктів досі залишаються актуальним завданням для органічної та медичної хімії. Широку варіативність у синтезі сульфоніл-та фосфорилзаміщених гетероциклів можуть забезпечити низькомолекулярні поліфункціональні речовини із сульфонільними та фосфорильними групами. У цьому огляді висвітлено наявну інформацію стосовно біологічно активних гетероциклічних сполук, які були синтезовані на основі акрилонітрилів та енамінів ряду сульфонів, фосфіноксидів та фосфонатів.

show abstract

Synthesis of C-heteryl-substituted aminomethylphosphonic acids derivatives

Cited by 4 publications

References 9 publications

Carbonic Anhydrase Inhibition with Sulfonamides Incorporating Pyrazole- and Pyridazinecarboxamide Moieties Provides Examples of Isoform-Selective Inhibitors

Carbonic Anhydrase Inhibition with Sulfonamides Incorporating Pyrazole- and Pyridazinecarboxamide Moieties Provides Examples of Isoform-Selective Inhibitors

Recyclization of 5‐Amino‐ oxazoles as a Route to new Functionalized Heterocycles (Developments of V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine)

α(β)-Sulfonyl(phosphoryl)acrylonitriles and enamines in the synthesis of biologically active heterocycles

Contact Info

Product

Resources

About