cyclohexylamines

Summary

Summary: A family of alicyclic hydrocarbons containing an amine group with the general formula R-C6H10NH2.

Top Publications

  1. Beppu T, Shirahata A, Takahashi N, Hosoda H, Samejima K. Specific depletion of spermidine and spermine in HTC cells treated with inhibitors of aminopropyltransferases. J Biochem. 1995;117:339-45 pubmed
    ..This increase was partially due to the increase of half-life of the enzyme. Separate roles for spermidine and spermine in the biosynthesis of the enzyme protein were also suggested...
  2. Molina G, Vogt A, Bakan A, Dai W, Queiroz de Oliveira P, Znosko W, et al. Zebrafish chemical screening reveals an inhibitor of Dusp6 that expands cardiac cell lineages. Nat Chem Biol. 2009;5:680-7 pubmed publisher
    ..This study highlights the power of in vivo zebrafish chemical screens to identify new compounds targeting Dusp6, a component of the FGF signaling pathway that has eluded traditional high-throughput in vitro screens...
  3. Nishimura K, Murozumi K, Shirahata A, Park M, Kashiwagi K, Igarashi K. Independent roles of eIF5A and polyamines in cell proliferation. Biochem J. 2005;385:779-85 pubmed
    ..The results show that a decrease in either active eIF5A or polyamines inhibits cell growth, indicating that eIF5A and polyamines are independently involved in cell growth..
  4. Hofer K, Grager B, Müller D, Rauber Lüthy C, Kupferschmidt H, Rentsch K, et al. Ketamine-like effects after recreational use of methoxetamine. Ann Emerg Med. 2012;60:97-9 pubmed publisher
    ..According to this case report, user Web reports, and the chemical structure, methoxetamine produces ketamine-like effects. Complete recovery can be expected with supportive care...
  5. Corazza O, Schifano F, Simonato P, Fergus S, Assi S, Stair J, et al. Phenomenon of new drugs on the Internet: the case of ketamine derivative methoxetamine. Hum Psychopharmacol. 2012;27:145-9 pubmed publisher
    ..Better international collaboration levels and novel forms of intervention are necessary to tackle this fast-growing phenomenon...
  6. Kaiser A, Gottwald A, Wiersch C, Lindenthal B, Maier W, Seitz H. Effect of drugs inhibiting spermidine biosynthesis and metabolism on the in vitro development of Plasmodium falciparum. Parasitol Res. 2001;87:963-72 pubmed
    ..falciparum. The use of specific inhibitors of spermidine metabolism might be a novel strategy for the design of new antimalarials, and suggests the occurrence of both enzymes in the parasite...
  7. Rosenbaum C, Carreiro S, Babu K. Here today, gone tomorrow…and back again? A review of herbal marijuana alternatives (K2, Spice), synthetic cathinones (bath salts), kratom, Salvia divinorum, methoxetamine, and piperazines. J Med Toxicol. 2012;8:15-32 pubmed publisher
    ..This paper discusses the background, pharmacology, clinical effects, detection, and management of synthetic cannabinoid, synthetic cathinone, methoxetamine, and piperazine exposures...
  8. Wood D, Davies S, Puchnarewicz M, Johnston A, Dargan P. Acute toxicity associated with the recreational use of the ketamine derivative methoxetamine. Eur J Clin Pharmacol. 2012;68:853-6 pubmed publisher
    ..We report here a case series of three individuals with acute toxicity related to the analytically confirmed use of methoxetamine...
  9. Chen J, Taipale J, Young K, Maiti T, Beachy P. Small molecule modulation of Smoothened activity. Proc Natl Acad Sci U S A. 2002;99:14071-6 pubmed
    ..The mechanistic differences between the Smo antagonists may be useful in the therapeutic manipulation of Hh signaling...

More Information

Publications62

  1. Shields J, Dargan P, Wood D, Puchnarewicz M, Davies S, Waring W. Methoxetamine associated reversible cerebellar toxicity: three cases with analytical confirmation. Clin Toxicol (Phila). 2012;50:438-40 pubmed publisher
    ..We report three cases that presented to hospital with acute neurological toxicity associated with analytically confirmed methoxetamine exposure...
  2. Yamada H, Furusho Y, Yashima E. Diastereoselective imine-bond formation through complementary double-helix formation. J Am Chem Soc. 2012;134:7250-3 pubmed publisher
    ..The second step involves formation of a preferred-handed complementary double helix assisted by the chiral amidine templates and determines the overall reaction rate and diastereoselectivity of the amine...
  3. Nowak G, Soundararajan S, Mestril R. Protein kinase C-? interaction with iHSP70 in mitochondria promotes recovery of mitochondrial function after injury in renal proximal tubular cells. Am J Physiol Renal Physiol. 2013;305:F764-76 pubmed publisher
    ..iHSP70 is recruited to mitochondria in response to PKC-? dephosphorylation and associates with and reactivates inactive PKC-?, which promotes the recovery of mitochondrial function, decreases RPTC death, and improves regeneration...
  4. Baud O, Gressens P. Hedgehog rushes to the rescue of the developing cerebellum. Sci Transl Med. 2011;3:105ps40 pubmed publisher
    ..In this issue of Science Translational Medicine, a pair of papers investigate--in patients and in a reliable animal model--the effects of glucocorticoids on cerebellar development after premature birth...
  5. Fang L, Gou S, Zhao J, Sun Y, Cheng L. Platinum(II) complexes with N-monoalkyl 1R,2R-diaminocyclohexane derivatives as carrier ligands and 3-hydroxycyclobutane-1,1-dicarboxylate as a leaving group: potent cytotoxicity and DNA binding ability. Eur J Med Chem. 2013;69:842-7 pubmed publisher
    ..The aqueous solubility of 1d is also improved, reaches 24.6 mg/mL. Furthermore, both docking study and agarose gel electrophoresis have confirmed the DNA-binding ability of 1d...
  6. Wang J, Li Q, Qi C, Liu Y, Ge Z, Li R. Primary 1,2-diamine catalysis III: an unexpected domino reaction for the synthesis of multisubstituted cyclohexa-1,3-dienamines. Org Biomol Chem. 2010;8:4240-2 pubmed publisher
    ..The first organocatalyzed multicomponent domino reactions of aryl ketones, aldehydes and malononitrile were carried out successfully to afford multisubstituted cyclohexa-1,3-dienamines in satisfactory yields...
  7. Abouelatta A, Sonk J, Hammoud M, Zurcher D, McKamie J, Schlegel H, et al. Synthesis, characterization, and theoretical studies of metal complexes derived from the chiral tripyridyldiamine ligand Bn-CDPy3. Inorg Chem. 2010;49:5202-11 pubmed publisher
  8. Rominger C, Bee W, Copeland R, Davenport E, Gilmartin A, Gontarek R, et al. Evidence for allosteric interactions of antagonist binding to the smoothened receptor. J Pharmacol Exp Ther. 2009;329:995-1005 pubmed publisher
    ..Our mechanism of action characterization of radioligand binding to Smo combined with functional data provides a better understanding of small-molecule interactions with Smo and their influence on the Hh pathway...
  9. Godenschwager P, Collum D. Lithium hexamethyldisilazide-mediated enolizations: influence of chelating ligands and hydrocarbon cosolvents on the rates and mechanisms. J Am Chem Soc. 2007;129:12023-31 pubmed
    ..The importance of LiHMDS-ketone complexes and the role of hydrocarbon cosolvents are discussed...
  10. González Vadillo A, Alvarez Valdés A, Moneo V, Blanco F, Díaz R, Carnero A, et al. Structure-activity relationship of new trans-platinum(II) and (IV) complexes with cyclohexylamine. Interference with cell cycle progression and induction of cell death. J Inorg Biochem. 2007;101:551-8 pubmed
    ..Mechanistically, the antitumor activity correlates with a blockade of the cell cycle in S phase and a complete abolishment of G2/M checkpoint arrest suggesting physical interaction of compound with DNA inhibiting S phase transition...
  11. Mahdi T, Heiden Z, Grimme S, Stephan D. Metal-free aromatic hydrogenation: aniline to cyclohexyl-amine derivatives. J Am Chem Soc. 2012;134:4088-91 pubmed publisher
    ..Hydrogenation of the N-bound phenyl rings of amines, imines, and aziridine is achieved in the presence of H(2) and B(C(6)F(5))(3), affording the corresponding N-cyclohexylammonium hydridoborate salts...
  12. Hu M, Tsai H. Reaction of cyclohexylamine with hypochlorite and enhancement of oxidation of plasma sulfhydryl groups by hypochlorite in vitro. Food Chem Toxicol. 1998;36:755-9 pubmed
    ..Because cyclamate is an important sweetener in many countries for people with diabetes mellitus, the possibility exists that CyhNH2 may enhance oxidation of important proteins by HOCl/OCl-...
  13. Shinzato C, Shoguchi E, Kawashima T, Hamada M, Hisata K, Tanaka M, et al. Using the Acropora digitifera genome to understand coral responses to environmental change. Nature. 2011;476:320-3 pubmed publisher
    ..The coral genome provides a platform for understanding the molecular basis of symbiosis and responses to environmental changes...
  14. Yusof A, Kothandaraman S, Zhang X, Saji M, Ringel M, Tweedle M, et al. Development of a calcium-sensing receptor molecular imaging agent. Surgery. 2013;154:1378-84; discussion 1384 pubmed publisher
    ..This compound appears to be appropriate for further development as a molecular imaging tool to enhance the surgical treatment of parathyroid disease and MTC. ..
  15. Takayama S, Renwick A, Johansson S, Thorgeirsson U, Tsutsumi M, Dalgard D, et al. Long-term toxicity and carcinogenicity study of cyclamate in nonhuman primates. Toxicol Sci. 2000;53:33-9 pubmed
  16. Elliott J, Castro J, Chicchi G, Cooper L, Dinnell K, Hollingworth G, et al. 4,4-Disubstituted cyclohexylamine NK(1) receptor antagonists I. Bioorg Med Chem Lett. 2002;12:1755-8 pubmed
  17. Gawronski J, Brzostowska M, Kwit M, Plutecka A, Rychlewska U. Rhombimines-cyclic tetraimines of trans-1,2-diaminocyclohexane shaped by the diaryl ether structural motif. J Org Chem. 2005;70:10147-50 pubmed
    ..reaction: see text] Rhombimines, chiral macrocyclic tetraimines, are preferentially formed because of the structural bias in the reaction of aromatic ether-linked dialdehydes with enantiomerically pure trans-1,2-diaminocyclohexane...
  18. Zaitseva J, Holland I, Schmitt L. The role of CAPS buffer in expanding the crystallization space of the nucleotide-binding domain of the ABC transporter haemolysin B from Escherichia coli. Acta Crystallogr D Biol Crystallogr. 2004;60:1076-84 pubmed
    ..Although the focus of these investigations was placed on HlyB-NBD, the strategy described here can be directly transferred to other proteins that display instability in solution...
  19. Mann S, Ploux O. 7,8-Diaminoperlargonic acid aminotransferase from Mycobacterium tuberculosis, a potential therapeutic target. Characterization and inhibition studies. FEBS J. 2006;273:4778-89 pubmed
    ..tuberculosis bioA gene, coding for DAPA AT. Reversal of the antibiotic effect was observed on the addition of biotin or DAPA. Thus, compound 1 specifically targets DAPA AT in vivo...
  20. Biftu T, Scapin G, Singh S, Feng D, Becker J, Eiermann G, et al. Rational design of a novel, potent, and orally bioavailable cyclohexylamine DPP-4 inhibitor by application of molecular modeling and X-ray crystallography of sitagliptin. Bioorg Med Chem Lett. 2007;17:3384-7 pubmed
    ..This was confirmed by structural analysis and the resulting analog 2a was synthesized and found to be a potent DPP-4 inhibitor (IC(50)=21 nM) with excellent in vivo activity and pharmacokinetic profile...
  21. Kennedy G. Review of the toxicology of three alkyl diamines. Drug Chem Toxicol. 2007;30:145-57 pubmed
    ..The main effects of this series of diamines appear related to their irritant properties, and attention needs to be paid to their delayed hypersensitivity potential...
  22. Louandre C, Ezzoukhry Z, Godin C, Barbare J, Mazière J, Chauffert B, et al. Iron-dependent cell death of hepatocellular carcinoma cells exposed to sorafenib. Int J Cancer. 2013;133:1732-42 pubmed publisher
    ..Ferroptosis could potentially become a goal for the medical treatment of HCC, thus opening new avenues for the optimization of the use of sorafenib in these tumors. ..
  23. Trela Z, Kleszczyńska H, Sarapuk J. Physiological and hemolytic toxicity of some aminophosphonates. Z Naturforsch C. 2001;56:838-42 pubmed
    ..Two modes of interaction are proposed...
  24. Lenz C, Boeckler F, Hubner H, Gmeiner P. Analogues of FAUC 73 revealing new insights into the structural requirements of nonaromatic dopamine D3 receptor agonists. Bioorg Med Chem. 2004;12:113-7 pubmed
    ..The electrostatic properties of the pharmacophoric pi-systems were visualized by diagnostic MEP maps...
  25. Yoshikawa K, Yokomizo A, Naito H, Haginoya N, Kobayashi S, Yoshino T, et al. Design, synthesis, and SAR of cis-1,2-diaminocyclohexane derivatives as potent factor Xa inhibitors. Part I: exploration of 5-6 fused rings as alternative S1 moieties. Bioorg Med Chem. 2009;17:8206-20 pubmed publisher
    ..Herein, we describe the synthesis and structure-activity relationship (SAR), together with the physicochemical properties and pharmacokinetic (PK) profiles of some prospective compounds...
  26. Mastrogiacomo A, Kohan S, Whitelegge J, Gundersen C. Intrinsic membrane association of Drosophila cysteine string proteins. FEBS Lett. 1998;436:85-91 pubmed
    ..Thus, we conclude that under physiological conditions csps are integral membrane proteins of secretory organelles, and that the cysteine string domain plays a vital role in the membrane association of these proteins...
  27. Spurgeon S, Coffey G, Fletcher L, Burke R, Tyner J, Druker B, et al. The selective SYK inhibitor P505-15 (PRT062607) inhibits B cell signaling and function in vitro and in vivo and augments the activity of fludarabine in chronic lymphocytic leukemia. J Pharmacol Exp Ther. 2013;344:378-87 pubmed publisher
    ..Our findings support the ongoing development of P505-15 as a therapeutic agent for B-cell malignancies. A dose finding study in healthy volunteers has been completed...
  28. de la Coba F, Aguilera J, De Galvez M, Alvarez M, Gallego E, Figueroa F, et al. Prevention of the ultraviolet effects on clinical and histopathological changes, as well as the heat shock protein-70 expression in mouse skin by topical application of algal UV-absorbing compounds. J Dermatol Sci. 2009;55:161-9 pubmed publisher
    ..Recent studies have focused on marine organisms as a source of natural bioactive molecules and some UV-absorbing algal compounds are under investigation as candidates for new natural sunscreens...
  29. Regino C, Torti S, Ma R, Yap G, Kreisel K, Torti F, et al. N-picolyl derivatives of Kemp's triamine as potential antitumor agents: a preliminary investigation. J Med Chem. 2005;48:7993-9 pubmed
  30. Chaki S, Funakoshi T, Hirota Okuno S, Nishiguchi M, Shimazaki T, Iijima M, et al. Anxiolytic- and antidepressant-like profile of ATC0065 and ATC0175: nonpeptidic and orally active melanin-concentrating hormone receptor 1 antagonists. J Pharmacol Exp Ther. 2005;313:831-9 pubmed
    ..These findings indicate that ATC0065 and ATC0175 are potent and orally active MCHR1 antagonists with anxiolytic and antidepressant activity in rodents...
  31. Geier J, Lessmann H, Hillen U, Jappe U, Dickel H, Koch P, et al. An attempt to improve diagnostics of contact allergy due to epoxy resin systems. First results of the multicentre study EPOX 2002. Contact Dermatitis. 2004;51:263-72 pubmed
    ..8%), followed by isophorone diamine (5.7%). No reactions were observed to several substances, the test concentration of which may have been too low and will be increased in the future...
  32. Librowski T, Vetulani J, Nalepa I. Carane derivative stereoisomers of different local anaesthetic and antiplatelet activity similarly potentiate forskolin-stimulated cyclic AMP response and bind to beta-adrenoceptors in the rat brain cortex. J Pharm Pharmacol. 2004;56:1429-34 pubmed
    ..The fact that the stereoisomers differed in both tests only slightly, if at all, suggests that their pharmacological effects are not related to the action on the beta-adrenoceptor/adenylate cyclase system...
  33. Shin K, Won B, Heo C, Kim H, Jang D, Park C, et al. BT-11 improves stress-induced memory impairments through increment of glucose utilization and total neural cell adhesion molecule levels in rat brains. J Neurosci Res. 2009;87:260-8 pubmed publisher
    ..In conclusion, BT-11 may be strongly effective against stress-induced amnesia in rats, through the combined effects of TMCA and other active components of BT-11...
  34. Wood D, Dargan P. Novel psychoactive substances: how to understand the acute toxicity associated with the use of these substances. Ther Drug Monit. 2012;34:363-7 pubmed publisher
  35. Zhong W, Williams M. Enantiospecific determination of PNU-83894 and its major metabolite, PNU-83892, in plasma, and its application to the characterization of the enantioselective pharmacokinetics of PNU-83894 in the dog. J Chromatogr A. 2000;871:201-6 pubmed
    ..The validity of this assay was also demonstrated by its application to the pharmacokinetic evaluation of PNU-83894 in the dog...
  36. Andre P, Morooka T, Sim D, Abe K, Lowell C, Nanda N, et al. Critical role for Syk in responses to vascular injury. Blood. 2011;118:5000-10 pubmed publisher
    ..Thus, Syk controls acute and long-term responses to arterial vascular injury. The therapeutic potential of Syk may be exemplary of a new class of antiatherothrombotic agents that target the interface between thrombosis and inflammation...
  37. Gárriz A, Gonzalez M, Marina M, Ruiz O, Pieckenstain F. Polyamine metabolism during sclerotial development of Sclerotinia sclerotiorum. Mycol Res. 2008;112:414-22 pubmed publisher
    ..The relationship between polyamine metabolism and sclerotial development, as well as the potential of polyamine biosynthesis inhibition as a strategy for the control of plant diseases caused by sclerotial fungi are discussed...
  38. Li G, Yu M, Lee W, Tsang M, Krishnan E, Weyand C, et al. Decline in miR-181a expression with age impairs T cell receptor sensitivity by increasing DUSP6 activity. Nat Med. 2012;18:1518-24 pubmed publisher
    ..DUSP6 is a potential intervention target for restoring T cell responses in the elderly, which may augment the effectiveness of vaccination...
  39. Azim A, Sharma S, Olsen C, Parmar V. Lipase catalysed synthesis of optically enriched alpha-haloamides. Bioorg Med Chem. 2001;9:1345-8 pubmed
    ..Candida antarctica lipase (CAL) was found to be a better catalyst over porcine pancreatic lipase (PPL) and Candida cylindracea lipase (CCL). The effect of different organic solvents was also studied...
  40. Balázs A, Hetényi A, Szakonyi Z, Sillanpää R, Fulop F. Solvent-enhanced diastereo- and regioselectivity in the Pd(II)-catalyzed synthesis of six- and eight-membered heterocycles via cis-aminopalladation. Chemistry. 2009;15:7376-81 pubmed publisher
    ..Additionally, a novel Pd(II)-mediated domino oxidation, oxidative amination reaction was discovered. Our experimental and theoretical findings suggest that the reactions proceed via a cis-aminopalladation mechanism...
  41. Jiang L, Wu T, Chen Y, Zhu J, Deng J. Asymmetric transfer hydrogenation catalysed by hydrophobic dendritic DACH-rhodium complex in water. Org Biomol Chem. 2006;4:3319-24 pubmed
    ..Moreover, the catalyst could be easily precipitated from the mixture by adding hexane and reused several times without affecting the high enantioselectivity...
  42. Gutierrez Castellanos N, Winkelman B, Tolosa Rodriguez L, Devenney B, Reeves R, De Zeeuw C. Size does not always matter: Ts65Dn Down syndrome mice show cerebellum-dependent motor learning deficits that cannot be rescued by postnatal SAG treatment. J Neurosci. 2013;33:15408-13 pubmed publisher
  43. Sergeeva E, Kopilov J, Goldberg I, Kol M. 2,2'-Bipyrrolidine versus 1,2-diaminocyclohexane as chiral cores for helically wrapping diamine-diolate ligands. Inorg Chem. 2009;48:8075-7 pubmed publisher
    ..In contrast, bipyrrolidine was found to be a perfect chiral motif for helical wrapping, and the corresponding diamine-diolate complexes were obtained as (enantiomerically pure) single diastereomers...
  44. Cho K, Ando M, Kobayashi K, Miyazoe H, Tsujino T, Ito S, et al. Design, synthesis and evaluation of a novel cyclohexanamine class of neuropeptide Y Y1 receptor antagonists. Bioorg Med Chem Lett. 2009;19:4781-5 pubmed publisher
    ..Modification of high-throughput screening hit compound 1 resulted in the identification of compound 3i, which displays potent Y1 activity and good selectivity towards hERG K(+) channel and serotonin transporter...
  45. Elbrønd Bek H, Wellejus A, Kelly N, Weidner M, Jørgensen S. 2-(Cyclohexylamino)-1-(4-cyclopentylpiperazin-1-yl)-2-methylpropan-1-one, a novel compound with neuroprotective and neurotrophic effects in vitro. Neurochem Int. 2011;59:821-9 pubmed publisher
    ..These results propose that amido-piperizine 1 may hold promise as a drug candidate for the treatment of stroke/traumatic brain injury or other neurodegenerative diseases...
  46. Danjo T, Eiraku M, Muguruma K, Watanabe K, Kawada M, Yanagawa Y, et al. Subregional specification of embryonic stem cell-derived ventral telencephalic tissues by timed and combinatory treatment with extrinsic signals. J Neurosci. 2011;31:1919-33 pubmed publisher
    ..We discuss a model of the antagonistic Fgf8 and Fgf15/19 signaling in rostral-caudal subpallial patterning and compare it with the roles of these molecules in cortical patterning...
  47. Löser R, Abbenante G, Madala P, Halili M, Le G, Fairlie D. Noncovalent tripeptidyl benzyl- and cyclohexyl-amine inhibitors of the cysteine protease caspase-1. J Med Chem. 2010;53:2651-5 pubmed publisher
    ..g., aldehyde) that normally confers high potency to cysteine protease inhibitors. Benzyl- or cyclohexylamines produced potent, reversible, and competitive inhibitors that were selective for caspase-1 (e.g...
  48. Iwaniuk D, Yearick Spangler K, Wolf C. Stereoselective UV sensing of 1,2-diaminocyclohexane isomers based on ligand displacement with a diacridylnaphthalene N,N'-dioxide scandium complex. J Org Chem. 2012;77:5203-8 pubmed publisher
    ..All three stereoisomers of 1,2-diaminocyclohexane can be differentiated using Sc[anti-(-)-1](2) in the same ligand displacement assay...
  49. Taylor A, Hansen L, Marzilli L. Biodistribution and renal excretion of isomers of the cationic tracer, (99m)Tc diaminocyclohexane (DACH): biodistribution of cationic renal tracers. Nucl Med Biol. 2001;28:299-302 pubmed
    ..Development of alternative cationic renal tracers is warranted...
  50. Brusova E, Kaverina N, Likhosherstov A. [Binding of dicyclohexylamide derivatives of N-substituted aminocarboxylic acids with muscarinic cholinoreceptors and beta-adrenoreceptors]. Eksp Klin Farmakol. 2002;65:39-41 pubmed
    ..The antimuscarinic activity of some NACA-DCHA derivatives, especially AL-275 and AL-315) may play a significant role in realization of the antiarrhythmic activity...
  51. Galanski M, Slaby S, Jakupec M, Keppler B. Synthesis, characterization, and in vitro antitumor activity of osteotropic diam(m)ineplatinum(II) complexes bearing a N,N-bis(phosphonomethyl)glycine ligand. J Med Chem. 2003;46:4946-51 pubmed
    ..Within the series of complexes under investigation, potency decreases depending on the coordinated amine ligand in the following order: trans-R,R-chxn > trans-S,S-chxn > NH(3) > or = cis-R,S-chxn > en...
  52. Gil Amado J, Gomez Jimenez M. Regulation of polyamine metabolism and biosynthetic gene expression during olive mature-fruit abscission. Planta. 2012;235:1221-37 pubmed publisher
  53. Kobayashi M, Takao K, Shiota Y, Sugita Y, Takahashi M, Nakae D, et al. Inhibition of putrescine aminopropyltransferase influences rat liver regeneration. Biol Pharm Bull. 2006;29:863-7 pubmed
    ..The results presented here will give a new aspect in the field of polyamine regulation to control cell growth in vivo...