Catalog number: 233661-54-6
Category: Main Product
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(1R,2R)-BOC-2-AMINOCYCLOHEXANE CARBOXYLIC ACID; (1R,2R)-BOC-ACHC; (1R,2R)-Boc-aminocyclohexane carboxylic acid
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1.Selective monoacylglycerol lipase inhibitors: antinociceptive versus cannabimimetic effects in mice.
Ignatowska-Jankowska B1, Wilkerson JL2, Mustafa M2, Abdullah R2, Niphakis M2, Wiley JL2, Cravatt BF2, Lichtman AH2. J Pharmacol Exp Ther. 2015 May;353(2):424-32. doi: 10.1124/jpet.114.222315. Epub 2015 Mar 11.
The endogenous cannabinoid 2-arachidonoylglycerol (2-AG) plays an important role in a variety of physiologic processes, but its rapid breakdown by monoacylglycerol lipase (MAGL) results in short-lived actions. Initial MAGL inhibitors were limited by poor selectivity and low potency. In this study, we tested JZL184 [4-nitrophenyl 4-[bis(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate] and MJN110 [2,5-dioxopyrrolidin-1-yl 4-(bis(4-chlorophenyl)methyl)piperazine-1-carboxylate], MAGL inhibitors that possess increased selectivity and potency, in mouse behavioral assays of neuropathic pain [chronic constriction injury (CCI) of the sciatic nerve], interoceptive cannabimimetic effects (drug-discrimination paradigm), and locomotor activity in an open field test. MJN110 (1.25 and 2.5 mg/kg) and JZL184 (16 and 40 mg/kg) significantly elevated 2-AG and decreased arachidonic acid but did not affect anandamide in whole brains. Both MAGL inhibitors significantly reduced CCI-induced mechanical allodynia with the following potencies [ED50 (95% confidence limit [CL]) values in mg/kg: MJN110 (0.
2.A new entry to asymmetric platinum(IV) complexes via oxidative chlorination.
Ravera M1, Gabano E, Pelosi G, Fregonese F, Tinello S, Osella D. Inorg Chem. 2014 Sep 2;53(17):9326-35. doi: 10.1021/ic501446b. Epub 2014 Aug 14.
Pt(IV) complexes are usually prepared by oxidation of the corresponding Pt(II) counterparts, typically using hydrogen peroxide or chlorine. A different way to synthesize asymmetrical Pt(IV) compounds is the oxidative chlorination of Pt(II) counterparts with N-chlorosuccinimide. The reaction between cisplatin cis-[PtCl2(NH3)2], carboplatin, cis-[PtCl2(dach)] and cis-[Pt(cbdc)(dach)] (cbdc = cyclobutane-1,1'-dicarboxylato; dach = cyclohexane-1R,2R-diamine) with N-chlorosuccinimide in ethane-1,2-diol was optimized to produce the asymmetric Pt(IV) octahedral complexes [PtA2Cl(glyc)X2] (A2 = 2 NH3 or dach; glyc = 2-hydroxyethanolato; X2 = 2 Cl or cbdc) in high yield and purity. The X-ray crystal structure of the [Pt(cbdc)Cl(dach)(glyc)] complex is also reported. Moreover, the oxidation method proved to be versatile enough to produce other mixed Pt(IV) derivatives varying the reaction medium. The two trichlorido complexes easily undergo a pH-dependent hydrolysis reaction, whereas the dicarboxylato compounds are stable enough to allow further coupling reactions for drug targeting and delivery via the glyc reactive pendant.
3.Antitumor platinum(II) complexes of N-monoalkyl 1R,2R-diamino-cyclohexanes with 3-(nitrooxy)cyclobutane-1,1-dicarboxylate as a leaving group.
Zhao J1, Gou S2, Xu G3, Cheng L3. Eur J Med Chem. 2014 Oct 6;85:408-17. doi: 10.1016/j.ejmech.2014.08.007. Epub 2014 Aug 5.
A series of platinum(II) complexes of N-monoalkyl-1R,2R-diaminocylclohexanes with 3-(nitrooxy)cyclobutane-1,1-dicarboxylate as a leaving group were synthesized and characterized by elemental analysis, IR, (1)H, (13)C and (195)Pt NMR spectroscopy together with ESI-MS spectrometer. In vitro cytotoxicity study on these complexes indicated they have considerable cytotoxicity against the tested cancer cell lines. Notably, complexes 2, 4, 6 and 8 showed high cytotoxicity against human A549 and HCT-116 cancer cell lines. The DNA binding of the platinum-based complexes 1 and 3-5 studied by agarose gel electrophoresis was in accordance with cytotoxicity to some extent. Reactions between the corresponding aqua analogues of the resulting complexes and glutathione (GSH) were studied by kinetics method under pseudo-first-order conditions using UV-Vis spectrophotometric technique. The results indicated that the introduction of alkyl moieties in 1R,2R-diaminocyclohexane (1R,2R-DACH) decreased the reaction rates of the aqua analogues of complexes 3-5 and GSH under the tested condition.
4.The effect of phytocannabinoids on airway hyper-responsiveness, airway inflammation, and cough.
Makwana R1, Venkatasamy R2, Spina D2, Page C2. J Pharmacol Exp Ther. 2015 Apr;353(1):169-80. doi: 10.1124/jpet.114.221283. Epub 2015 Feb 5.
Cannabis has been demonstrated to have bronchodilator, anti-inflammatory, and antitussive activity in the airways, but information on the active cannabinoids, their receptors, and the mechanisms for these effects is limited. We compared the effects of Δ(9)-tetrahydrocannabinol, cannabidiol, cannabigerol, cannabichromene, cannabidiolic acid, and tetrahydrocannabivarin on contractions of the guinea pig-isolated trachea and bronchoconstriction induced by nerve stimulation or methacholine in anesthetized guinea pigs following exposure to saline or the proinflammatory cytokine, tumor necrosis factor α (TNF-α). CP55940 (2-[(1R,2R,5R)-5-hydroxy-2-(3-hydroxypropyl) cyclohexyl]-5-(2-methyloctan-2-yl)phenol), a synthetic cannabinoid agonist, was also investigated in vitro. The cannabinoids were also evaluated on TNF-α- and lipopolysaccharide-induced leukocyte infiltration into the lungs and citric acid-induced cough responses in guinea pigs. TNF-α, but not saline, augmented tracheal contractility and bronchoconstriction induced by nerve stimulation, but not methacholine.
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