67003-49-0Relevant academic research and scientific papers
Photoredox/Nickel Dual Catalytic Cross-Coupling of Potassium Thiomethyltrifluoroborates with Aryl and Heteroaryl Bromides
Townsend, Katherine,Huestis, Malcolm P.,Tellis, John C.
, p. 6937 - 6942 (2021/05/29)
The cross-coupling of S-aryl and S-alkyl potassium thiomethyltrifluoroborates with aryl and heteroaryl bromides is reported via photoredox/nickel dual catalysis. The transformation is achieved under mild conditions with commercially available or readily prepared, air stable reagents and affords benzylthioether products in moderate to good yields with good functional group tolerance. A practical and improved synthesis of potassium thiomethyltrifluoroborates is also reported that affords access to previously undescribed reagents.
SUBSTITUTED PYRIDINES AS INHIBITORS OF DNMT1
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Page/Page column 1033, (2018/01/20)
The invention is directed to substituted pyridine derivatives. Specifically, the invention is directed to compounds according to Formula (Iar): (Iar) wherein Yar, X1ar, X2ar, R1ar, R2ar, R3ar, R4ar and R5ar are as defined herein; or a pharmaceutically acceptable salt or prodrug thereof. The compounds of the invention are selective inhibitors of DNMT1 and can be useful in the treatment of cancer, pre-cancerous syndromes, beta hemoglobinopathy disorders, sickle cell disease, sickle cell anemia, and beta thalassemia, and diseases associated with DNMT1 inhibition. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting DNMT1 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.
Synthesis of dibenzo[c,e]oxepin-5(7H)-ones from benzyl thioethers and carboxylic acids: Rhodium-catalyzed double C-H activation controlled by different directing groups
Zhang, Xi-Sha,Zhang, Yun-Fei,Li, Zhao-Wei,Luo, Fei-Xian,Shi, Zhang-Jie
supporting information, p. 5478 - 5482 (2015/04/27)
A rhodium(III)-catalyzed cross-coupling of benzyl thioethers and aryl carboxylic acids through the two directing groups is reported. Useful structures with diverse substituents were efficiently synthesized in one step with the cleavage of four bonds (C-H, C-S, O-H) and the formation of two bonds (C-C, C-O). The formed structure is the privileged core in natural products and bioactive molecules. This work highlights the power of using two different directing groups to enhance the selectivity of a double C-H activation, the first of such examples in cross-oxidative coupling.
Reparametrization and/or determination of hammett, inductive, mesomeric and aise substituent constants for five substituents: N+(CH 3)3, CH2N+(CH3) 3, CH2Py+, CH2SO2CH 3 and PO(OCH3)2
Picha, Jan,Cibulka, Radek,Liska, Frantisek,Parik, Patrik,Pytela, Oldrich
, p. 2239 - 2252 (2007/10/03)
Ten meta- and para-substituted benzoic acids with substituants N +(CH3)3, CH2N+(CH 3)3, CH2Py+, CH2SO 2CH3 and PO(OCH3)2 were synthesized. Dissociation constants of these acids were determined in five solvents (water, ethanol, methanol, N,N-dimethylformamide, dimethyl sulfoxide) at 25°C. Dissociation constants of benzoic acid derivatives with other substituents H, CH3, NHCOCH3, OCH3, F, Cl, Br, I, COCH 3, CN, NO2, SO2CH3 were taken from the literature (calibration set). Substituent constants σm, σp, σI, σR, and σi for substituents N+(CH3)3, CH2N+(CH3)3, CH2Py +, CH2SO2CH3, and PO(OCH 3)2 were calculated by non-linear and PLS (partial least-square method with latent variables) calibration in three correlation models using the calibration set. Nonlinear regression appears more suitable and more universal than PLS calibration. The advantage of nonlinear regression is its independence on possibly missing data in the given solvent, evaluation of precision (standard deviation), the accessibility of necessary software, and easy calculation. However, in contrast to PLS calibration, this procedure fails in calculation of substituent constants with description of properties of substituents (substituent constants σI, σR). The obtained values of substituent constants are in good agreement with those published in the literature.
Design and synthesis of benzoic acid derivatives as influenza neuraminidase inhibitors using structure-based drug design
Chand, Pooran,Babu, Yarlagadda S.,Bantia, Shanta,Chu, Naiming,Cole, L. Brent,Kotian, Pravin L.,Laver, W. Graeme,Montgomery, John A.,Pathak, Ved P.,Petty, Sandra L.,Shrout, David P.,Walsh, David A.,Walsh, Gerald M.
, p. 4030 - 4052 (2007/10/03)
A series of 94 benzoic acid derivatives was synthesized and tested for its ability to inhibit influenza neuraminidase. The enzyme-inhibitor complex structure was determined by X-ray crystallographic analysis for compounds which inhibited the enzyme. The most potent compound tested in vitro, 5 (4- (acetylamino)-3-guanidinobenzoic acid), had an IC50 = 2.5 x 10-6 M against N9 neuraminidase. Compound 5 was oriented in the active site of the neuraminidase in a manner that was not predicted from the reported active site binding of GANA (4) with neuraminidase. In a mouse model of influenza, 5 did not protect the mice from weight loss due to the influenza virus when dosed intranasally.
