Syntheses of antibacterial 2,4-diamino-5-benzylpyrimidines. Ormetoprim and trimethoprim

Manchand, Percy S.; Rosen, Perry; Belica, Peter S.; Oliva, Gloria; Perrotta, A.; Wong, Harry S.

doi:10.1021/jo00039a006

Cited by 32 publications

(10 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In industrial manufacturing, the synthesis of TMP is a complex process, and potential impurities probably still remain in TMP. 6,7 The purity of TMP is critical for its further application. In order to obtain high-purity products, it is necessary to apply solubility data to the industrial process.…”

Section: Introductionmentioning

confidence: 99%

“…The solubility of drugs plays an important role in pharmaceutical and industrial processes, such as crystallization, isolation, and purification. In industrial manufacturing, the synthesis of TMP is a complex process, and potential impurities probably still remain in TMP. , The purity of TMP is critical for its further application. In order to obtain high-purity products, it is necessary to apply solubility data to the industrial process.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Solubility of Trimethoprim in Selected Pure Solvents and (Water + Ethanol/2-Propanol) Mixed-Solvent Systems

Yin

Liu

et al. 2015

J. Chem. Eng. Data

View full text Add to dashboard Cite

Trimethoprim (TMP) is an important antibacterial synergist in human and veterinary medicine. In this work, the solubilities of TMP in five pure solvents (ethanol, water, ethyl acetate, acetonitrile, and 2-propanol) and two binary mixtures (ethanol + water and 2-propanol + water) were measured by an equilibrium method over the temperature range from (293.15 to 322.65) K under atmospheric pressure. The experimental results show that in the pure solvents the solubility of TMP increases with increasing temperature, and the solubility decreases in the following order: ethanol > acetonitrile > 2-propanol > ethyl acetate > water. In the mixed solvents, the solubility of TMP increases with increasing temperature and mass fraction of the organic solvent. The mole-fraction solubility of TMP was observed to be the highest in the mixed solvent 50% ethanol/2-propanol, and the lowest mole-fraction solubility of TMP was found in water. Three correlating models (the modified Apelblat equation, the λh equation, and the ideal model) were used to correlate the experimental solubility values in the pure solvents, and four models (the modified Apelblat equation, the λh equation, the ideal model, and the CNIBS/R-K model) were applied to correlate the experimental solubilities in the mixed solvents. All of these thermodynamic models gave satisfactory correlation results, with the modified Apelblat equation showing better fitting degree than the other three equations. Furthermore, the standard molar enthalpy of the TMP during the dissolving process (ΔH sol °) was also determined in this work, and the results show that the dissolution process is endothermic.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Solubility of Trimethoprim in Selected Pure Solvents and (Water + Ethanol/2-Propanol) Mixed-Solvent Systems

Yin

Liu

et al. 2015

J. Chem. Eng. Data

View full text Add to dashboard Cite

show abstract

“…Можно заключить, что классические аналоги будут использовать теже самые клеточные транспортные системы что и сама фолиевая кислота или, например, 3, и метаболизироваться до полиглутамат производных (Схема 2), а неклассические липофильные антифолаты не требовательны к транспортным системам и не будут превращаться в полиглутаматы [28]. Соединениями, принадлежащими к группе неклассических препаратов, являются производными пиридо [2,3-d]пиримидина [29,30,31,32], например пиритрексим (10, PTx) [33] и триметриксат (11,TMQ) [34], а также пиримидина, такие как триметоприм (12, TMP) [35], пириметамин (13, PyR) [36] и метоприм (14, DDMP) [37].…”

Section: Coo -unclassified

Antifolates for Cancer Chemotherapy. Part I

Bacherikov¹

2014

Odesa National University Herald. Chemistry

View full text Add to dashboard Cite

Посвящаю памяти моего учителя профессора Андрея Ивановича Греня В обзоре рассмотрены структуры основных противораковых антифолатов, их внутриклеточные ферментные цели, механизмы их противоопухолевого действия. Подробно обсуждены фолатные антиметаболиты, полученные в последнее десятилетие и тенденции в поиске высокоэффективных ингибиторов метаболических путей фолиевой кислоты. Рассмотрены достоинства и ограничения антифолатов, которые могут быть использованы в дизайне новых препаратов противоопухолевой химиотерапии. Ключевые слова: антифолаты, антиметаболиты, противораковая химиотерапия. Открытие роли фолиевой кислоты (1) в клеточном метаболизме привело к пониманию того, что антагонисты фолиевой кислоты могут служить лекарствами для лечения бактериальныых инфекций и злокачественных новообразований. Фолиевая кислота (1) также известна как витамин b 9 или фолацин, и в живых организмах существует в виде аниона фолата. Молекула 1 состоит из гетероциклического фрагмента птеридина соединенного с остатком п-аминобензойной кислоты, в свою очередь присоединенный пептидной связью с α-аминогруппой остатка глутаминовой кислоты, которых может быть несколько. Все живые клетки используют производные фолиевой кислоты для биосинтеза тимидина, пуринов и метионина (Схема 1). Рис. 1. Фолиевая кислота и некоторые первичные фолатные антиметаболиты.

show abstract

“…3,4,5-Trimethoxybenzaldehyde (TMBA), a pharmaceutical intermediate, is widely used to prepare the antibacterial agent trimethoprim [1]. Trimethoprim is used solely, or in combination with sulfamethoxazole to treat a wide range of bacterial infections in humans and poultry [2].…”

Section: Introductionmentioning

confidence: 99%

Treatment of 3,4,5-trimethoxybenzaldehyde and Di-bromo-aldehyde manufacturing wastewater by the coupled Fenton pretreatment and UASB reactor with emphasis on optimization and chemicals analysis

Hong

Jin

et al. 2015

Separation and Purification Technology

View full text Add to dashboard Cite

Syntheses of antibacterial 2,4-diamino-5-benzylpyrimidines. Ormetoprim and trimethoprim

Cited by 32 publications

References 0 publications

Solubility of Trimethoprim in Selected Pure Solvents and (Water + Ethanol/2-Propanol) Mixed-Solvent Systems

Solubility of Trimethoprim in Selected Pure Solvents and (Water + Ethanol/2-Propanol) Mixed-Solvent Systems

Antifolates for Cancer Chemotherapy. Part I

Treatment of 3,4,5-trimethoxybenzaldehyde and Di-bromo-aldehyde manufacturing wastewater by the coupled Fenton pretreatment and UASB reactor with emphasis on optimization and chemicals analysis

Contact Info

Product

Resources

About