111079-46-0Relevant academic research and scientific papers
Organocatalyzed Enantioselective Michael Addition of 2-Hydroxypyridines and α,β-Unsaturated 1,4-Dicarbonyl Compounds
Wu, Yu-Chun,Jhong, Yi,Lin, Hui-Jie,Swain, Sharada Prasanna,Tsai, Hui-Hsu Gavin,Hou, Duen-Ren
, p. 4966 - 4982 (2019)
The framework of 2-pyridones is prevalent in biologically and medicinally important molecules. Here we report that chiral N-substituted 2-pyridones were prepared by enantioselective, organocatalytic aza-Michael additions of halogenated 2-hydroxypyridines (pyridin-2(1H)-ones) to α,β-unsaturated-1,4-dketones or 1,4-ketoesters. The reactions were optimized by the choice of solvents and systematic screening of Cinchona alkaloid-based bifunctional catalysts to achieve excellent yields and enantioselectivities (up to 98% yield and >99% ee). Density functional theory calculations provided rationales for the observed enantioselectivity. Formal synthesis of a human rhinovirus protease inhibitor was achieved using the chiral Michael adduct generated by this method. (Figure presented.).
A nitrogen oxide C2 - bit hydroxylated method (by machine translation)
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Paragraph 0031; 0032; 0033; 0034; 0035; 0036-0038; 0117-0122, (2017/05/19)
The present invention relates to nitrogen oxide C2 - bit hydroxylated method, in particular under reflux conditions in dichloroethane, three pyrrole alkyl bromide (PyBrop) [...] phosphate, sodium acetate, water and nitrogen oxides produced by the reaction of hydroxyl-substituted product. The process has simple operation, mild condition, high reaction selectivity, substrate wide applicability, high yield and the like. The application for the first time using this method to synthesize a series of 2 - hydroxyquinoline, 2 - hydroxy pyridine and 1 - hydroxy isoquinoline compound, in the establishment of the compounds of the library synthesis application have broad prospects. (by machine translation)
Reaction and separation methods
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, (2008/06/13)
A method of separating compounds that includes the steps of: tagging at least a first organic compound with a first tagging moiety to result in a first tagged compound; tagging at least a second organic compound with a second tagging moiety different from
Camptothecin analogs and methods of preparation thereof
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, (2008/06/13)
A compound has the formula in racemic form, enantiomerically enriched form or enantiomerically pure form. R6is preferably —Si(R8R9R10) or —(R7)Si(R8R9R10), wherein R7is an alkylene group, an alkenylene group, or an alkynylene group; and R8, R9and R10are independently a C1-10alkyl group, a C2-10alkenyl group, a C2-10alkynyl group, an aryl group or a —(CH2)NR11group, wherein N is an integer within the range of 1 through 10 and R11is a hydroxy group, alkoxy group, an amino group, an alkylamino group, a dialkylamino group, a halogen atom, a cyano group, —SRcor a nitro group. R1-R can be broadly substituted. R5is preferably a C1-10alkyl group, an alkenyl group, an alkynyl group, or a benzyl group. R13is preferably H, F or —CH3. R16is R16is —C(O)Rfor H. The E-ring (the lactone ring) may be opened. A method of synthesis of compound (1) and intermediates in the synthesis thereof are provided.
Novel benzofuran and benzothiophene biphenyls as inhibitors of protein tyrosine phosphatase 1B with antihyperglycemic properties
Malamas, Michael S.,Sredy, Janet,Moxham, Christopher,Katz, Alan,Xu, Weixin,McDevitt, Robert,Adebayo, Folake O.,Sawicki, Diane R.,Seestaller, Laura,Sullivan, Donald,Taylor, Joseph R.
, p. 1293 - 1310 (2007/10/03)
Insulin resistance in the liver and peripheral tissues, together with a pancreatic cell defect, are the common causes of Type 2 diabetes. It is now appreciated that insulin resistance can result from a defect in the insulin receptor signaling system, at a site post binding of insulin to its receptor. Protein tyrosine phosphatases (PTPases) have been shown to be negative regulators of the insulin receptor. Inhibition of PTPases may be an effective method in the treatment of Type 2 diabetes. We have identified two novel series of benzofuran/benzothiophene biphenyl oxo-acetic acids and sulfonyl- salicylic acids as potent inhibitors of PTP1B with good oral antihyperglycemic activity. To assist in the design of these inhibitors, crystallographic studies have attempted to identify enzyme inhibitor interactions. Resolution of crystal complexes has suggested that the inhibitors bind to the enzyme active site and are held in place through hydrogen bonding and van der Waals interactions formed within two hydrophobic pockets. In the oxo-acetic acid series, hydrophobic substitutents at position-2 of the benzofuran/benzothiophene biphenyl framework interacted with Phe182 of the catalytic site and were very critical to the intrinsic activity of the molecule. The hydrophobic region of the catalytic-site pocket was exploited and taken advantage by hydrophobic substituents at either the α-carbon or the ortho aromatic positions of the oxo-acetic acid moiety. Similar ortho aromatic substitutions on the salicylic acid-type inhibitors had no effect, primarily due to the different orientation of these inhibitors in the catalytic site. The most active inhibitors of both series inhibited recombinant human PTP1B with phosphotyrosyl dodecapeptide TRDI(P)YETD(P)Y(P)YRK as the source of the substrate with IC50 values in the range of 20-50 nM. Compound 68 was one of the most active compounds in vivo, normalizing plasma glucose levels at the 25 mg/kg dose (po) and the 1 mg/kg dose (ip). Compound 68 was also selective against several other PTPases.
Camptothecin analogs and methods of preparation thereof
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, (2008/06/13)
A compound and a method of synthesizing a compound having the following general formula (1): wherein R1 and R2 are independently the same or different and are hydrogen, an alkyl group, an alkenyl group, a benzyl group, an alkynyl group, an alkoxy group, a
