cas 67478-50-6, 1-TRITYLIMIDAZOLE-2-CARBOXALDEHYDE

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OGA INHIBITOR COMPOUNDS
The present invention relates to O-GIcNAc hydrolase (OGA) inhibitors of formula (I). The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention and treatment of disorders in which inhibition of OGA is beneficial, such as tauopathies in particular Alzheimer's disease or progressive supranuclear palsy; and neurodegenerative diseases accompanied by a tau pathology, in particular amyotrophic lateral sclerosis or frontotemporal lobe dementia caused by C90RF72 mutations.
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Page/Page column 72

(2020/01/11)

Optimization of diarylpentadienones as chemotherapeutics for prostate cancer
Our earlier studies indicate that (1E,4E)-1,5-bis(1-alkyl-1H-imidazol-2-yl)penta-1,4-diene-3-ones and (1E,4E)-1,5-bis(1-alkyl-1H-benzo[d]imidazol-2-yl)penta-1,4-diene-3-ones exhibit up to 121-fold greater antiproliferative potency than curcumin in human p
Patanapongpibul, Manee,Zhang, Changde,Chen, Guanglin,Guo, Shanchun,Zhang, Qiang,Zheng, Shilong,Wang, Guangdi,Chen, Qiao-Hong
p. 4751 - 4760
(2018/08/21)

Synthesis and Biological Evaluation of Imidazole-Bearing α-Phosphonocarboxylates as Inhibitors of Rab Geranylgeranyl Transferase (RGGT)
Rab geranylgeranyl transferase (RGGT) is an interesting therapeutic target, as it ensures proper functioning of Rab GTPases, a class of enzymes responsible for the regulation of vesicle trafficking. Relying on our previous studies, we synthesized a set of new α-phosphonocarboxylic acids as potential RGGT inhibitors, with emphasis on the elaboration of imidazole-containing analogues. We identified two compounds with activity similar to that of previously reported RGGT inhibitors, showing structural similarity to imidazo[1,2-a]pyridine-containing analogues in terms of their substitution pattern. Interestingly, analogues of the N-series, derived from another phosphonocarboxylate RGGT inhibitor, 2-fluoro-3-(1H-imidazol-1-yl)-2-phosphonopropanoic acid, turned out to be inactive in our model, indicating that an additional substituent localized at positions C2 or C4 of the imidazole ring, may adversely affect the potency against the targeted enzyme.
Joachimiak, ?ukasz,Marchwicka, Aleksandra,Gendaszewska-Darmach, Edyta,B?a?ewska, Katarzyna M.
p. 842 - 851
(2018/03/09)

Identification of a novel class of covalent modifiers of hemoglobin as potential antisickling agents
Aromatic aldehydes and ethacrynic acid (ECA) exhibit antipolymerization properties that are beneficial for sickle cell disease therapy. Based on the ECA pharmacophore and its atomic interaction with hemoglobin, we designed and synthesized several compounds-designated as KAUS (imidazolylacryloyl derivatives)-that we hypothesized would bind covalently to βCys93 of hemoglobin and inhibit sickling. The compounds surprisingly showed weak allosteric and antisickling properties. X-ray studies of hemoglobin in complex with representative KAUS compounds revealed an unanticipated mode of Michael addition between the β-unsaturated carbon and the N-terminal αVal1 nitrogen at the α-cleft of hemoglobin, with no observable interaction with βCys93. Interestingly, the compounds exhibited almost no reactivity with the free amino acids, l-Val, l-His and l-Lys, but showed some reactivity with both glutathione and l-Cys. Our findings provide a molecular level explanation for the compounds biological activities and an important framework for targeted modifications that would yield novel potent antisickling agents.
Omar,Mahran,Ghatge,Chowdhury,Bamane,El-Araby,Abdulmalik,Safo
p. 6353 - 6370
(2015/06/08)

Synthesis, structure-activity relationship studies, and identification of novel 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine derivatives as dual orexin receptor antagonists. Part 1
A novel series of non-peptidic OX1R/OX2R orexin receptor antagonists was prepared by heterocyclic replacement of the dimethoxyphenyl moiety contained in the tetrahydroisoquinoline core skeleton of almorexant. Introduction of substituted imidazole moieties delivered potent dual orexin receptor antagonists with nanomolar potency for hOX1R and hOX2R suitable for further fine-tuning. The preparation of these novel orexin receptor antagonists and the outcome of preliminary structure-activity relationship studies are described in this communication.
Sifferlen, Thierry,Koberstein, Ralf,Cottreel, Emmanuelle,Boller, Amandine,Weller, Thomas,Gatfield, John,Brisbare-Roch, Catherine,Jenck, Francois,Boss, Christoph
p. 2212 - 2216
(2013/04/23)

Asymmetric Copper(II)-catalysed nitroaldol (Henry) reactions utilizing a chiral C1-symmetric dinitrogen ligand
A series of stable chiral C1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensation of chiral amines [(-)-exo-bornylamine or (+)-(1S,2S,5R)-menthylamine] with various substituted imidazolecarbaldehydes. With the assistance of base, the ligand L1 in combination with CuCl2·2H2O (2.5 mol-% or 5.0 mol-%) can efficiently promote nitroaldol (Henry) reactions between a variety of aldehydes and nitromethane. Both aromatic and aliphatic aldehydes were tolerated in our catalytic system, affording the expected nitroalcohol products in high yields (up to 97%) and with good enantioselectivities (up to 96%) under mild reaction conditions. A series of chiral C1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensations of chiralamines with various substituted imidazolecarbaldehydes. The ligand L1 in conjunction with CuCl2·2H2O can efficiently promote nitroaldol (Henry) reactions between various aldehydes and nitromethane in high yields (up to 97%) and with good enantioselectivities (up to 96%).
Zhou, Yirong,Gong, Yuefa
experimental part
p. 6092 - 6099
(2011/11/29)

Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors
A new series of potential GABA uptake inhibitors starting from of 1H-imidazol-4-ylacetic acid with the carboxylic acid side chain originating from different positions and varying in length have been synthesized and tested for the inhibitory potency at the
Hack, Silke,W?rlein, Babette,H?fner, Georg,Pabel, J?rg,Wanner, Klaus T.
experimental part
p. 1483 - 1498
(2011/05/11)

5,6,7,8-TETRAHYDRO-IMIDAZO[1,5-A]PYRAZINE DERIVATIVES
The invention relates to 5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine derivatives of formula (I),wherein X represents CH2 or O; R1 represents a phenyl group, which group is independently mono-, di-, or tri-substituted wherein the substituents are independently selected from the group consisting of (C1-4)alkyl, (C1-4)alkoxy, halogen, cyano, trifluoromethoxy and trifluoromethyl; R2 represents (C1-4)alkyl, (C1-4)alkoxy, (C2-4)alkenyl, halogen, cyano, hydroxymethyl, trifluoromethyl, C(O)NR5R6 or cyclopropyl; R3 represents (C1-4)alkyl, (C1-4)alkoxy-methyl or halogen; R4 represents (C1-4)alkyl; R5 represents hydrogen or (C1-4)alkyl; and R6 represents hydrogen or (C1-4)alkyl. The invention also relates to pharmaceutically acceptable salts of such compounds; and to the use of such compounds as medicaments; especially as orexin receptor antagonists.
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Page/Page column 67-68

(2008/12/06)

Chemokine receptor binding heterocyclic compounds with enhanced efficacy
The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).
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(2008/06/13)

Chemokine receptor binding heterocyclic compounds with enhanced efficacy
The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).
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Page/Page column 19-20

(2010/02/03)

1-(Aromatic- or heteroaromatic-substituted)-3-(heteroaromatic substituted)-1,3-propanediones and uses thereof
Certain 1-(aromatic- or heteroaromatic-substituted-3-(heteroaromatic substituted)-1,3-propanediones are described as inhibitors of HIV integrase and inhibitors of HIV replication. These compounds are useful in the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.
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Page 34

(2010/02/06)

N-(imidazolylalkyl)substituted cyclic amines as histamine-H3 agonists or antagonists
The present invention discloses novel N(imidazolylalkyl)-substituted cyclic amine compounds which have excellent histamine-H3 receptor antagonist activity as well as methods for preparing such compounds. In another embodiment, the invention discloses phar
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(2008/06/13)

Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles
A new protocol using radical cyclisation has been developed for the synthesis of [1,2-c]-fused imidazoles and [1,2-a]-fused pyrroles. The intermediate nucleophilic N-alkyl radicals, generated using Bu3SnH from N- (ω-bromoalkyl) or N-[ω-(phenylselanyl)alkyl] imidazoles and pyrroles, undergo regio-selective radical cyclisalion onto the azole rings followed by oxidative re-aromatisation.
Aldabbagh, Fawaz,Russell Bowman,Mann, Emma,Slawin, Alexandra M.Z.
p. 8111 - 8128
(2007/10/03)

Condensed thiazole derivative, production process thereof and pharmaceutical composition thereof
Condensed thiazole derivatives useful as 5-HT3 receptor agonists are provided and can be represented by the following formula (I) or a pharmaceutically acceptable salt thereof, a process for the production thereof and a pharmaceutical composition thereof: STR1 wherein R, A, L1, L2, L, and R1 -R6 are defined herein and Im represents a group of the formula: STR2
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(2008/06/13)

Synthesis of Aryl 2-(2-Imidazolyl)ethyl Ketones
The Claisen-Schmidt condensation of 1-(triphennylmethyl)-2-imidazolecarboxaldehyde with acetophenones yielded 1-aryl-3-propen-1-ones 7.Selective catalytic hydrogenation over platinum of 7 furnished 1-aryl-3-(2-imidazolyl)
Abdelaal, Salma M.,Kim, Jang-Woo,Bauer, Ludwig
p. 903 - 906
(2007/10/02)

Imidazole-containing inhibitors of farnesyl protein transferase
Inhibition of farnesyl transferase, which is an enzyme involved in ras oncogene expression, is effected by compounds of the formula their enantiomers, diastereomers, and pharmaceutically acceptable salts, prodrugs, and solvates, wherein:, G is G1 is G2 is or -NR10-CH(Q1)-;, J, K and L are each, independently, N, NR9, O, S or CR10 with the provisos that only one of the groups J, K and L can be O or S, and at least one of the groups J or L must be N, NR9, O or S to form a fused five-membered heteroring; the bond between J and K or K and L may also form one side of a phenyl ring fused to the fused five-membered heteroring;, Q is aryl;, Q1, A1 and A2 are each, independently, H, alkyl, substituted alkyl, phenyl or substituted phenyl;, G3 is R11, -C(O)OR11, -C(O)NR11R12, 5-tetrazolyl, -C(O)N(R13)OR11, -C(O)NHSO2R14 or -CH2OR11;, G4 is attached at the 1, 2, 4 or 5 position and optionally substituted, at any of the available position or positions on the ring, with halo, alkyl or substituted alkyl having 1 to 20 carbon atoms, alkoxy, aryl, aralkyl, hydroxy, alkanoyl, alkanoyloxy, amino, alkylamino, dialkylamino, alkanoylamino, thiol, alkylthio, alkylthiono, alkylsulfonyl, sulfonamido, nitro, cyano, carboxy, carbamyl, N-hydroxycarbamyl, N-alkylcarbamyl, N-dialkylcarbamyl, alkoxycarbonyl, phenyl, substituted phenyl, or a combinaton of these groups;, Y and Z are each, independently, -CH2- or -C(O)-;, R1 - R14 are each, independently, H or alkyl having 1 to 20 carbon atoms;, R7, R8 and R14 may also be aryl or aralkyl, and R3, R9, R11, R12 and R13 may also be aralkyl;, m, n and p are each, independently, 0 or an integer from 1 to 2;, q is 0 or an integer from 1 to 4; and, the dotted line represents an optional double bond.
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(2008/06/13)

4-Lithio-1-tritylimidazole as a Synthetic Intermediate. Synthesis of Imidazole-4-carboxaldehyde
Reaction of 4-iodo-1-tritylimidazole with n-butyllithium at -79 deg, followed by rapid quenching of the reaction mixture with DMF, gives good yields of 1-tritylimidazole-4(5)-carboxaldehyde, the isolation of which demonstrates the intermediacy of 4-lithio-1-tritylimidazole.This species should be destabilized by repulsive interaction of the negative charge on C-4 with the adjacent lone pair electrons on N-3 (the ALP effect).The isolation of 1-tritylimidazole-4(5)-carboxaldehyde in good yield and the versatility of the aldehyde functionality make 4-lithio-1-tritylimidazole a useful synthetic intermediate.
Kirk, Kenneth L.
p. 57 - 59
(2007/10/02)