cas 25115-74-6, 4-CYANO-4-PHENYLCYCLOHEXANONE

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Antimalarial activity of 2,6-dibenzylidenecyclohexanone derivatives
Malaria remains one of the deadliest infectious diseases worldwide and continues to infect hundreds of millions of individuals each year. Here we report the discovery and derivatization of a series of 2,6-dibenzylidenecyclohexanones targeting the chloroquine-sensitive 3D7 strain of Plasmodium falciparum. While the initial lead compound displayed significant toxicity in a human cell proliferation assay, we were able to identify a derivative with no detectable toxicity and sub-micromolar potency.
Eagon, Scott,Hammill, Jared T.,Fitzsimmons, Kasey,Sienko, Natalie,Nguyen, Brandon,Law, Jarvis,Manjunath, Aashrita,Wilkinson, Steven P.,Thompson, Kara,Glidden, Julia Elizabeth,Rice, Amy L.,Falade, Mofolusho O.,Kimball, Joshua J.,DiBernardo, Celine,Guy, R. Kiplin
(2021)
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Conversion of Simple Cyclohexanones into Catechols
A novel I2-catalyzed direct conversion of cyclohexanones to substituted catechols under mild and simple conditions has been described. This novel transformation is remarkable with the multiple oxygenation and dehydrogenative aromatization processes enabled just by using DMSO as the solvent, oxidant, and oxygen source. This metal-free and simple system demonstrates a versatile protocol for the synthesis of highly valuable substituted catechols and therefore streamlines the synthesis and modification of biologically important molecules for drug discovery.
Liang, Yu-Feng,Li, Xinyao,Wang, Xiaoyang,Zou, Miancheng,Tang, Conghui,Liang, Yujie,Song, Song,Jiao, Ning
supporting information
p. 12271 - 12277
(2016/09/28)

Discovery of C-(1-aryl-cyclohexyl)-methylamines as selective, orally available inhibitors of dipeptidyl peptidase IV
The successful launches of dipeptidyl peptidase IV (DPP IV) inhibitors as oral anti-diabetics warrant and spur the further quest for additional chemical entities in this promising class of therapeutics. Numerous pharmaceutical companies have pursued their proprietary candidates towards the clinic, resulting in a large body of published chemical structures associated with DPP IV. Herein, we report the discovery of a novel chemotype for DPP IV inhibition based on the C-(1-aryl-cyclohexyl)-methylamine scaffold and its optimization to compounds which selectively inhibit DPP IV at low-nM potency and exhibit an excellent oral pharmacokinetic profile in the rat. 2014 Elsevier Ltd. All rights reserved.
Namoto, Kenji,Sirockin, Finton,Ostermann, Nils,Gessier, Francois,Flohr, Stefanie,Sedrani, Richard,Gerhartz, Bernd,Trappe, J?rg,Hassiepen, Ulrich,Duttaroy, Alokesh,Ferreira, Suzie,Sutton, Jon M.,Clark, David E.,Fenton, Garry,Beswick, Mandy,Baeschlin, Daniel K.
p. 731 - 736
(2014/02/14)

Synthesis and optimization of novel 4,4-disubstituted cyclohexylbenzamide derivatives as potent 11β-HSD1 inhibitors
The synthesis and SAR of a series of 4,4-disubstituted cyclohexylbenzamide inhibitors of 11β-HSD1 are described. Optimization rapidly led to potent, highly selective, and orally bioavailable inhibitors demonstrating efficacy in both rat and non-human primate ex vivo pharmacodynamic models.
Sun, Daqing,Wang, Zhulun,Caille, Seb,Degraffenreid, Michael,Gonzalez-Lopez De Turiso, Felix,Hungate, Randall,Jaen, Juan C.,Jiang, Ben,Julian, Lisa D.,Kelly, Ron,McMinn, Dustin L.,Kaizerman, Jacob,Rew, Yosup,Sudom, Athena,Tu, Hua,Ursu, Stefania,Walker, Nigel,Willcockson, Maren,Yan, Xuelei,Ye, Qiuping,Powers, Jay P.
body text
p. 405 - 410
(2011/02/27)

Optimization of novel di-substituted cyclohexylbenzamide derivatives as potent 11β-HSD1 inhibitors
Novel 4,4-disubstituted cyclohexylbenzamide inhibitors of 11β-HSD1 were optimized to account for liabilities relating to in vitro pharmacokinetics, cytotoxicity and protein-related shifts in potency. A representative compound showing favorable in vivo pharmacokinetics was found to be an efficacious inhibitor of 11β-HSD1 in a rat pharmacodynamic model (ED50 = 10 mg/kg).
McMinn, Dustin L.,Rew, Yosup,Sudom, Athena,Caille, Seb,DeGraffenreid, Michael,He, Xiao,Hungate, Randall,Jiang, Ben,Jaen, Juan,Julian, Lisa D.,Kaizerman, Jacob,Novak, Perry,Sun, Daqing,Tu, Hua,Ursu, Stefania,Walker, Nigel P.C.,Yan, Xuelei,Ye, Qiuping,Wang, Zhulun,Powers, Jay P.
scheme or table
p. 1446 - 1450
(2010/01/16)

SUBSTITUTED 4-AMINOCYCLOHEXANE DERIVATIVES
The invention relates to compounds that have an affinity to the μ-opioid receptor and the ORL 1-receptor, methods for their production, medications containing these compounds and the use of these compounds for the treatment of pain and other conditions.
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(2009/10/06)

Spirocyclic Azaindole Derivatives
The invention relates to substituted azaindole derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted azaindole derivatives for producing medicaments.
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Page/Page column 9

(2009/07/03)

Potent bradykinin B1 receptor antagonists: 4-Substituted phenyl cyclohexanes
Selective bradykinin (BK) B1 receptor antagonists have been shown to be antinociceptive in animal models and could be novel therapeutic agents for the treatment of pain and inflammation. Elucidation of the structure-activity relationships of the biphenyl moiety of the lead compound 1 provided a potent new structural class of BK B1 receptor antagonists.
Su, Dai-Shi,Lim, John L.,Markowitz, M. Kristine,Wan, Bang-Lin,Murphy, Kathy L.,Reiss, Duane R.,Harrell, C. Meacham,O'Malley, Stacy S.,Ransom, Rick W.,Chang, Raymond S.L.,Pettibone, Douglas J.,Tang, Cuyue,Prueksaritanont, Thomayant,Freidinger, Roger M.,Bock, Mark G.
p. 3006 - 3009
(2008/02/04)

Chemoenzymatic synthesis of a non-peptide tachykinin NK-2 antagonist
The synthesis of a tachykinin NK-2 antagonist (S)-11 has been carried out in four steps starting from the the (S)-(+)-enol acetate 3, which was obtained in 100% e.e. by resolution of the racemic ester with Pseudomonas fluorescens lipase. The absolute configuration of the enol acetate (+)-3 was confirmed by X-ray analysis of the camphanyl derivative 13. (C) 2000 Elsevier Science Ltd.
Carnell, Andrew J.,Hernandez, Maria Luisa Escudero,Pettman, Alan,Bickley, Jamie F.
p. 6929 - 6933
(2007/10/03)

Desymmetrisation of prochiral ketones by catalytic enantioselective hydrolysis of their enol esters using enzymes
Desymmetrisation of 4-cyano-4-phenylcyclohexanone 1 has been achieved by enzyme-catalysed enantioselective alcoholysis with n-butanol of the derived racemic enol acetate 2 in tetrahydrofuran. The absolute configuration of the enol aceate (-)-(S)-2 (100% e.e.) obtained was determined by X-ray analysis of the camphanyl derivative 7.
Carnell, Andrew J.,Barkley, Jim,Singh, Amarjit
p. 7781 - 7784
(2007/10/03)

Phenyl-1,2,3,4-tetrahydrocarbazoles and use thereof
This application relates to phenyl-substituted 1,2,3,4-tetrahydrocarbazoles and to their use as anti-depressant agents useful in the treatment of mental depression of either endogenous or reactive nature.
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(2008/06/13)

Synthesis and Reactivity of 4-Phenylisoquinuclidines
Several approaches to the synthesis of the 2-alkyl-4-phenylisoquinuclidines 14 and 15, the 3,4-diphenylisoquinuclidines 22-24 and of 6-oxo-4-phenyl-3-isoquinuclidone (43) are described.The structure of the products of hydrolysis of 7-phenyl-1,4-dioxaspirodecanecarboxamide (36) were determined by spectroscopy and degradative reactions.
Schneider, Woldemar,Krombholz, Gottfried
p. 487 - 498
(2007/10/02)

Analgetic compounds, compositions and process of treatment
Novel compounds of the formula: STR1 wherein R1 is a variable consisting of hydrogen, alkyl of from 1 to 8 carbon atoms, CH2 -alkenyl wherein alkenyl is from 2 to 4 carbon atoms, inclusive, cycloalkyl of from 3 to 6 carbon atoms, inclusive, cycloalkylmethyl of from 3 to 6 carbon atoms, inclusive; R2 is a variable consisting of hydrogen, alkyl of from 1 to 8 carbon atoms, inclusive, with the proviso that R1 and R2 cannot both be hydrogen at the same time; Y is a variable consisting of alkyl of from 1 to 4 carbon atoms, inclusive, halogen, trifluoromethyl, hydroxy, alkanoyloxy from 2 to 5 carbon atoms, inclusive, alkoxy of from 1 to 4 carbon atoms, inclusive, cycloalkyloxy of from 3 to 6 carbon atoms, inclusive, benzyloxy; m is an integer 0, 1, 2; R5 is a variable consisting of hydrogen and alkyl of from 1 to 4 carbon atoms, inclusive; R3 is a variable consisting of alkyl of from 1 to 4 carbon atoms, inclusive; R4 is a variable consisting of alkyl of from 1 to 4 carbon atoms, inclusive, CH2 -alkenyl wherein alkenyl is of from 2 to 4 carbon atoms, inclusive, and arylalkyl wherein alkyl is from 1 to 4 carbon atoms, inclusive, and aryl is STR2 WHEREIN Y' is CF3, halogen, alkyl of 1 to 4 carbon atoms, inclusive, and alkoxy of from 1 to 4 carbon atoms, inclusive; and R3 and R4 when taken together with the nitrogen atom to which they are attached can form saturated heterocycles of from 5 to 7 ring members, a second hetero atom of said ring can be oxygen or nitrogen, e.g., morpholine, piperazine, and said heterocycles can be monosubstituted having a total of up to 9 carbon atoms, with the proviso that when STR3 is pyrrolidinyl, then m = 1, 2, having analgetic activity in humans and animals are prepared in unit dosage forms. The compositions are useful in relieving pain by administering orally, parenterally, and rectally to humans and animals.
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(2008/06/13)

4-Amino-4-phenylcyclohexanone ketal compositions and process of use
A class of new 4-amino-4-arylcyclohexanones, their ketals, and acid addition salts have been synthesized and found to be useful for relieving pain in animals. Their analgesic activity appears to be of high order, and in addition some exhibit narcotic antagonist activity that is useful in modifying the cardiovascular, respiratory, and behavioral depression caused by other analgesics. Several show mixed analgesic and narcotic antagonist activity. Preferred compounds of the class are 4-(m-hydroxyphenyl)-4-dimethylaminocyclohexanone ethylene ketal, and 4-(m-hydroxyphenyl)-4-(n-butylmethylamino)cyclohexanone ethylene ketal as free bases and as their hydrochloride salts. Processes for synthesis and intermediates are described. Unit dosage forms and therapeutic treatments are disclosed.
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(2008/06/13)

Indazole derivatives, processes for making the same and pharmaceutical compositions
This invention relates to indazole derivatives, to processes for their preparation and to pharmaceutical compositions containing them. More specifically this invention relates to 4, 5, 6, 7-tetrahydroindazoles bearing at the 3-position an amino substituent. This invention also relates to processes for producing the same which include the steps of condensing a substituted cyclohexanone with a secondary amine, reacting the thus formed enamine either with an isocyanate or thiocyanate or with phosgene imonium salt and cyclizing the intermediate compound with a hydrazino derivative. The compounds of the invention have therapeutic utility, namely as a means for controlling fertility in mammals.
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(2008/06/13)

4-Arylcyclohexylamines
The invention relates to novel 4-hydroxymethyl(acyloxymethyl and methyl)-4-arylcyclohexylamines embraced by the formula SPC1 Wherein Ar is an aromatic ring selected from the group consisting of phenyl and naphthyl, each of which has from zero through three substituents independently selected from the group consisting of fluorine, chlorine, bromine, lower alkyl of one through three carbon atoms, lower alkoxy of one through three carbon atoms, and lower alkylthio of one through three carbon atoms; Z is selected from the group consisting of hydrogen, hydroxy and lower acyloxy of one through four carbon atoms; ? is a generic expression denoting cis and trans stereoconfiguration and mixtures thereof, with the proviso that when the stereoconfiguration of the linkage connecting the cyclohexane ring and CH2 Z is cis to the amino group, the linkage connecting the cyclohexane and Ar rings is trans, and vice versa; R1 is selected from the group consisting of hydrogen and lower alkyl of one through three carbon atoms; R2 is selected from the group consisting of hydrogen, lower alkyl of one through three carbon atoms, EQU1 WHEREIN N IS 2 THROUGH 5 AND Ar has the same meaning as above; R1 and R2 taken together with --N is a saturated heterocyclic amino radical selected from the group consisting of unsubstituted and substituted pyrrolidino, piperidino, hexamethylenimino, morpholino and piperazino; and pharmacologically acceptable acid addition salts thereof. It also relates to intermediates and processes for the preparation of the aforesaid novel compounds (I) and novel derivatives thereof. The administration to humans and animals of the novel compounds (I) depresses their central nervous systems and lowers their blood pressures.
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(2008/06/13)