14289-44-2Relevant articles and documents
Mono-β-cyclodextrin as an Efficient Glyoxalase Mimic
Tamagaki, Seizo,Katayama, Atsushi,Maeda, Masahiko,Yamamoto, Noritaka,Tagaki, Waichiro
, p. 507 - 512 (1994)
Trifunctional mono-β-cyclodextrin (MACD) has been prepared and used as a gloxalase model.When 2-naphthylglyoxal (NAGO) is employed as a diagnostic substrate, MACD shows an overall activity greater than the reference compo
α-Ketocarboxylic acid-based inhibitors of protein tyrosine phosphatases
Chen, Yen Ting,Onaran,Doss, Christopher J.,Seto, Christopher T.
, p. 1935 - 1938 (2001)
A series of aryl α-ketocarboxylic acids was synthesized and investigated as inhibitors for the protein tyrosine phosphatase from Yersinia enterocolitica. IC50 values for these compounds range from 79 to 2700 μM. Larger aromatic groups, and aromatic groups with high electron density, lead to more potent inhibitors. In general, the related aryl α-hydroxycarboxylic acids show lower activity.
Photocatalytic Carbinol Cation/Anion Umpolung: Direct Addition of Aromatic Aldehydes and Ketones to Carbon Dioxide
Okumura, Shintaro,Uozumi, Yasuhiro
supporting information, p. 7194 - 7198 (2021/09/22)
We have developed a new photocatalytic umpolung reaction of carbonyl compounds to generate anionic carbinol synthons. Aromatic aldehydes or ketones reacted with carbon dioxide in the presence of an iridium photocatalyst and 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzimidazole (DMBI) as a reductant under visible-light irradiation to furnish the corresponding α-hydroxycarboxylic acids through nucleophilic addition of the resulting carbinol anions to electrophilic carbon dioxide.
Synthesis of novel proxyphylline derivatives with dual Anti-Candida albicans and anticancer activity
Borowiecki, Pawe?,Wińska, Patrycja,Bretner, Maria,Gizińska, Ma?gorzata,Koronkiewicz, Miros?awa,Staniszewska, Monika
, p. 307 - 333 (2018/03/21)
Three out of 16 newly synthesized 1,3-dimethylxanthine derivatives (proxyphylline analogues) exhibited consistencies between antifungal and anticancer properties. Proxyphylline possessing 1-(10H-phenothiazin-10-yl)propan-2-yl (6) and polybrominated benzimidazole (41) or benzotriazole moiety (42) remained selectively cidal against Candida albicans (lg R ≥ 3 at conc. of 31, 36 and 20 μM, respectively) however not against normal mammalian Vero cell line in vitro (IC50 ≥ 280 μM) and Galleria mellonella in vivo. These compounds also displayed moderate antineoplastic activity against human breast adenocarcinoma (MCF-7) cell line (EC50 = 80 μM) and high against peripheral blood T lymphoblast (CCRF-CEM) (EC50 = 6.3–6.5 μM). In addition, 6 and 42 exerted: (1) dual activity against fungal adhesion and damage mature biofilm; (2) necrosis of planktonic cells due to loss of membrane function and of structural integrity; (3) biochemical (inhibition of sessile cell respiration) and morphological changes in cell wall polysaccharide contents. Therefore, leading proxyphylline derivatives can be employed to prevent cancer-associated biofilm Candida infections.
The Synthesis of Chiral α-Aryl α-Hydroxy Carboxylic Acids via RuPHOX-Ru Catalyzed Asymmetric Hydrogenation
Guo, Huan,Li, Jing,Liu, Delong,Zhang, Wanbin
, p. 3665 - 3673 (2017/09/11)
A ruthenocenyl phosphino-oxazoline-ruthenium complex (RuPHOX?Ru) catalyzed asymmetric hydrogenation of α-aryl keto acids has been successfully developed, affording the corresponding chiral α-aryl α-hydroxy carboxylic acids in high yields and with up to 97% ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 5000 S/C) and the resulting products can be transformed to several chiral building blocks, biologically active compounds and chiral drugs. (Figure presented.).
Chemoenzymatic Preparation of Enantiomerically Enriched (R)-(–)-Mandelic Acid Derivatives: Application in the Synthesis of the Active Agent Pemoline
Potera?a, Marcin,Dranka, Maciej,Borowiecki, Pawe?
, p. 2290 - 2304 (2017/05/01)
The enantioselective resolution of several racemic derivatives of mandelic acid methyl ester catalyzed by lipases from Pseudomonas fluorescens (Amano AK) or Burkholderia cepacia (Amano PS-C II and Amano PS-IM) has been achieved. A gram-scale lipase-mediated kinetic resolution approach has been developed that allows the facile synthesis of the corresponding methyl (R)-(–)-mandelates with excellent enantiomeric excesses (up to >99 % ee) and reaction enantioselectivity (E values up to >200). The dopaminergic agent pemoline, used in the treatment of attention-deficit hyperactivity disorder (ADHD) and narcolepsy, was synthesized with 98 % ee in a straightforward route by condensing the prepared methyl (R)-(–)-mandelate with guanidine hydrochloride under basic conditions. The desired (R)-(+)-pemoline in optically pure form (>99 % ee) was obtained after two recrystallizations from ethanol. However, it was confirmed by chiral HPLC that optically active pemoline undergoes racemization in methanol solution.
Development of a potent 2-oxoamide inhibitor of secreted phospholipase A2 guided by molecular docking calculations and molecular dynamics simulations
Vasilakaki, Sofia,Barbayianni, Efrosini,Leonis, Georgios,Papadopoulos, Manthos G.,Mavromoustakos, Thomas,Gelb, Michael H.,Kokotos, George
, p. 1683 - 1695 (2016/04/05)
Inhibition of group IIA secreted phospholipase A2 (GIIA sPLA2) has been an important objective for medicinal chemists. We have previously shown that inhibitors incorporating the 2-oxoamide functionality may inhibit human and mouse GIIA sPLA2s. Herein, the development of new potent inhibitors by molecular docking calculations using the structure of the known inhibitor 7 as scaffold, are described. Synthesis and biological evaluation of the new compounds revealed that the long chain 2-oxoamide based on (S)-valine GK241 led to improved activity (IC50 = 143 nM and 68 nM against human and mouse GIIA sPLA2, respectively). In addition, molecular dynamics simulations were employed to shed light on GK241 potent and selective inhibitory activity.
Carboxylation with CO2 via brook rearrangement: Preparation of α-hydroxy acid derivatives
Mita, Tsuyoshi,Higuchi, Yuki,Sato, Yoshihiro
, p. 14 - 17 (2014/01/23)
In the presence of CsF, a wide range of α-substituted α-siloxy silanes were carboxylated under a CO2 atmosphere (1 atm) via Brook rearrangement. A variety of α-substituents including aryl, alkenyl, and alkyl groups were tolerated to afford α-hydroxy acids in moderate-to-high yields. One-pot synthesis from aldehydes using PhMe2SiLi and CO 2 was also possible, providing α-hydroxy acids without the isolation of an α-hydroxy silane.
Amberlyst A-26: An efficient and reusable heterogeneous catalyst for a one-pot oxidation-Cannizarro reaction
Shen, Ming-Gui,Shang, Shi-Bin,Song, Zhan-Qian,Wang, Dan,Rao, Xiao-Ping,Gao, Hong,Liu, He
, p. 51 - 52 (2013/03/29)
Amberlyst A-26 catalyses the efficient synthesis of α-hydroxy- arylacetic acids from aryl methyl ketones in the presence of SeO2. After simple separation, the catalyst does not lose its activity and can be reused without significant loss in activity for at least four cycles.
PDE10 INHIBITORS AND RELATED COMPOSITIONS AND METHODS
-
Page/Page column 8, (2010/03/02)
Compounds that inhibit PDE10 are disclosed that have utility in the treatment of a variety of conditions, including (but not limited to) psychotic, anxiety, movement disorders and/or neurological disorders such as Parkinson's disease, Huntington's disease, Alzheimer's disease, encephalitis, phobias, epilepsy, aphasia, Bell's palsy, cerebral palsy, sleep disorders, pain, Tourette's syndrome, schizophrenia, delusional disorders, drug-induced psychosis and panic and obsessive-compulsive disorders. Pharmaceutically acceptable salts, stereoisomers, solvates and prodrugs of the compounds are also provided. Also disclosed are compositions containing a compound in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use thereof for inhibiting PDE10 in a warm-blooded animal in need of the same.
