103-80-0Relevant articles and documents
Process development and pilot-scale synthesis of new cyclization conditions of substituted phenylacetamides to tetrahydroisoquinoline-2-ones using Eaton's reagent
Ulysse, Luckner G.,Yang, Qiang,McLaws, Mark D.,Keefe, Daniel K.,Guzzo, Peter R.,Haney, Brian P.
, p. 225 - 228 (2010)
Tetrahydroisoquinoline is a ubiquitous structural framework presented in numerous pharmacologically relevant molecules. Although accessible by the Pictet-Spengler cyclization, conditions commonly used for such cyclizations are often difficult to implement on scale. Herein, we report the development of a scaleable approach utilizing Eaton's reagent for the cyclization of substituted phenylacetamide analogues to tetrahydroisoquinoline-2-one. The development, optimization, and safety hazard evaluations, which outline the benefits and ease of workup of this new process, are discussed.
Direct meta-C?H Perfluoroalkenylation of Arenes Enabled by a Cleavable Pyrimidine-Based Template
Brochetta, Massimo,Borsari, Tania,Bag, Sukdev,Jana, Sadhan,Maiti, Siddhartha,Porta, Alessio,Werz, Daniel B.,Zanoni, Giuseppe,Maiti, Debabrata
, p. 10323 - 10327 (2019)
The development of efficient and mild methods for the synthesis of organofluorine compounds is of foremost interest in various fields of chemistry. A direct pyrimidine-based selective meta-C?H perfluoroalkenylation of arenes involving several commercially
Synthesis and antimicrobial activity of new 2-[p-substituted-benzyl]-5- [substituted-carbonyl-amino]benzoxazoles
Yildiz-Orena, Ilkay,Tekiner-Gulbas, Betul,Yalcin, Ismail,Temiz-Arpaci, Ozlem,Aki-Sener, Esin,Altanlar, Nurten
, p. 402 - 410 (2004)
A series of 23 new 2-[p-substituted-benzyl]-5-[p-substituted-phenyl/benzyl- carbonylamino]benzoxazole derivatives has been synthesized by reacting 5-amino-2-[p-substituted-benzyl]benzoxazoles with the appropriate carboxylic acid chlorides. The structures of the synthesized compounds were confirmed by IR and 1H-NMR spectral data. Antimicrobial activities of the compounds were investigated using the twofold serial dilution technique against two gram-positive and two gram-negative bacteria and three Candida species in comparison with standard drugs. Microbiological results indicated that the newly synthesized 2-[p-substituted-benzyl]-5-[p-substituted-phenyl/benzyl- carbonylamino]benzoxazole derivatives (3-25) possessed a broad spectrum of activity, showing MIC values of 6.25-200 μg/mL against the gram-positive and gram-negative microorganisms tested. Moreover, they showed significant antifungal activity with MIC values of 3.12-100 μg/mL against the Candida species tested. Especially, with a MIC value of 3.12 μg/mL, 2-benzyl-5-[p-bromobenzyl-carbonylamino]benzoxazole 9 displayed the same activity against C. glabrata as the standard drug myconazol.
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Carpino
, p. 96 (1957)
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Comparative reactivity of N′-(5-benzoyl/ethoxycarbonyl)thiazol-2-yl- N,N-dimethylformamidines with ketenes
Singh, Parvesh,Marwaha, Alka,Singh, Harmeet,Mahajan, Mohinder P.
, p. 11999 - 12005 (2005)
The comparative account of the reactivities of N′-[(5-benzoyl and ethoxycarbonyl)thiazol-2-yl]-N,N-dimethylformamidines (1a and 1b), tremendously influenced by the electronic nature of the substituents on C-5 of the thiazolic ring with various monosubstituted and conjugated ketenes is reported herein. The DA cycloadditions of the dienyl pyrimidinone 3h with both symmetrical as well as unsymmetrical dienophiles leading to the formation of various thiazolic pyrimidinone derivatives are also reported.
Photochemistry of N-hydroxypyridine-2-thione derivatives: Involvement of the 2-pyridylthiyl radical in the radical chain reaction mechanism
Aveline, Béatrice M.,Kochevar, Irene E.,Redmond, Robert W.
, p. 9699 - 9708 (1995)
The primary and subsequent photochemistry of four N-hydroxypyridine-2-thione esters has been investigated by laser flash photolysis (λexc = 355 nm). A simple, high-yield synthetic method is given for their preparation with high purity. UV irradiation of these ester compounds was shown to lead specifically to the formation of benzyl, diphenylmethyl, tert-butyl, and benzoyloxyl radicals in addition to the 2-pyridylthiyl radical. In all cases, the initial photoinduced nitrogen-oxygen bond cleavage was found to occur in high quantum yield (ΦN-O ≈ 0.5). The radical species generated by this process (2-pyridylthiyl radical and carbon-centered or oxygen-centered radicals) were characterized and their reactivity toward several radical scavengers has been studied. An efficient delayed depletion of the N-hydroxypyridine-2-thione esters was also observed, leading to overall bleaching quantum yields, ΦBl, close to unity. We have demonstrated that the delayed consumption of ground-state ester was due to the reaction of the 2-pyridylthiyl radical with its precursor, occurring with a rate constant, kr, of 3-4 × 109 M-1 s-1. This reaction, hitherto never proposed, leads to the formation of 2,2′-dipyridyl disulfide and further release of propagating radicals.
One-step Conversion of Amides and Esters to Acid Chlorides with PCl3
Li, Fangshao,Wu, Xiaofang,Guo, Fengzhe,Tang, Zi-Long,Xiao, Jing
supporting information, p. 4314 - 4317 (2021/07/16)
A general and efficient iodine-promoted chlorination of amides and esters with phosphorus trichloride is described. For the first time. Various inactivated amides including secondary and tertiary amides were directly converted to the corresponding acid chlorides in one-step. The substrate scope of methyl esters including aromatic and aliphatic esters was also explored under this system. This method is simple, scalable and wide in scope, which provides an approach to preparation of these acid chlorides.
Achiral Derivatives of Hydroxamate AR-42 Potently Inhibit Class i HDAC Enzymes and Cancer Cell Proliferation
Tng, Jiahui,Lim, Junxian,Wu, Kai-Chen,Lucke, Andrew J.,Xu, Weijun,Reid, Robert C.,Fairlie, David P.
, p. 5956 - 5971 (2020/06/05)
AR-42 is an orally active inhibitor of histone deacetylases (HDACs) in clinical trials for multiple myeloma, leukemia, and lymphoma. It has few hydrogen bond donors and acceptors but is a chiral 2-arylbutyrate and potentially prone to racemization. We report achiral AR-42 analogues incorporating a cycloalkyl group linked via a quaternary carbon atom, with up to 40-fold increased potency against human class I HDACs (e.g., JT86, IC50 0.7 nM, HDAC1), 25-fold increased cytotoxicity against five human cancer cell lines, and up to 70-fold less toxicity in normal human cells. JT86 was ninefold more potent than racAR-42 in promoting accumulation of acetylated histone H4 in MM96L melanoma cells. Molecular modeling and structure-activity relationships support binding to HDAC1 with tetrahydropyran acting as a hydrophobic shield from water at the enzyme surface. Such potent inhibitors of class I HDACs may show benefits in diseases (cancers, parasitic infections, inflammatory conditions) where AR-42 is active.