cas 120241-79-4, Pyridine, 3-(1H-1,2,3-triazol-4-yl)- (9CI)

Articles about 120241-79-4Total 16 be found

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Two new mononuclear zinc(II) and cadmium(II) coordination polymers based on 4-(3-pyridyl)-2H-1,2,3-triazole: Syntheses, structures, theoretical and fluorescent properties
Two new d10 metal coordination polymers (CPs), [Zn(L)NO3]n (1) and [Cd(L)I2]n (2) (L = 4-(3-Pyridyl)-2H-1,2,3-triazole), have been designed and synthesized from ZnII/CdII ions and the rigid L ligand. The CPs 1 and 2 have been structurally characterized by single-crystal X-ray diffraction analyses, elemental analysis, IR spectroscopy, powder X-ray diffraction (PXRD) and thermal gravimetric analyses (TGA). CP 1 exhibits a hcb (3,3)-connected 2D network with the point symbol (63) and further forms a supramolecular 3D structure via hydrogen bonds. CP 2 reveals a 1D straight chain constructed by units of [Cd(1)N2I4] and hydrogen bonding leads to the formation of supramolecular 3D system. In addition, time-dependent density functional theory calculations with B3LYP functional were performed on L, CPs 1 and 2 to rationalize their experimental absorption spectra. The luminescence properties of L, CPs 1 and 2 in solid-state and different solvents have been also investigated.
Zhao, Rong,Li, Yan-Jun,Chen, Yun-Feng,Cong, Ye,Zhang, Jiang,Dong, Zhi-Jun,Yuan, Guan-Ming,Cui, Zheng-Wei,Li, Xuan-Ke
p. 44 - 51
(2019)
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Palladium-catalyzed one-pot synthesis of 4-Aryl-1 H-1,2,3-triazoles from anti-3-Aryl-2,3-dibromopropanoic acids and sodium azide
4-Aryl-1H-1,2,3-triazoles were synthesized from anti-3-aryl-2,3- dibromopropanoic acids and sodium azide by a one-pot method using N,N-dimethylformamide as solvent in the presence of tris(dibenzylideneacetone) dipalladium(0) [Pd2(dba)3] and Xantphos. Georg Thieme Verlag Stuttgart.
Zhang, Wensheng,Kuang, Chunxiang,Yang, Qing
p. 283 - 287
(2010)
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The synthesis of 1,2,3-triazoles from nitroalkenes - Revisited
Nitroalkenes or vicinal acetoxy nitro derivatives undergo a clean reaction with sodium azide in hot dimethyl sulfoxide to give the corresponding 1,2,3-triazoles in good yield. Georg Thieme Verlag Stuttgart.
Quiclet-Sire, Beatrice,Zard, Samir Z.
p. 3319 - 3326
(2005)
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Metal-Free Cascade [4 + 1] Cyclization Access to 4-Aryl- NH-1,2,3-triazoles from N-Tosylhydrazones and Sodium Azide
A molecular iodine-mediated coupling cyclization reaction for the synthesis of 4-aryl-NH-1,2,3-triazoles has been developed from N-tosylhydrazones and sodium azide. This metal-free cascade [4 + 1] cyclization reaction could rapidly synthesize valuable com
Shu, Wen-Ming,Zhang, Xun-Fang,Zhang, Xiang-Xiang,Li, Min,Wang, An-Jing,Wu, An-Xin
p. 14919 - 14925
(2019/11/11)

Synthesis method of NH-1,2,3-triazole compound
The invention relates to a synthesis method of a NH-1,2,3-triazole compound. The synthesis method is characterized by comprising the following steps that aldehyde, a nitro compound, sodium azide, a solvent and an additive react for 1-8 hours through a one-pot method at the temperature of 80 DEG C to 150 DEG C, and after reacting is finished, NH-1,2,3-triazole can be prepared through aftertreatment. According to the synthesis method, aldehyde, the nitro compound and sodium azide which are cheap and easy to obtain are adopted as raw materials, and the NH-1,2,3-triazole compound can be conveniently prepared from the three components. Compared with an existing method, the method has the advantages that the raw materials are low in cost, simple and easy to obtain, operation is easy and convenient, and the reaction efficiency is high.
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Paragraph 0024

(2017/07/20)

Method for preparing 4-aryl-NH-1,2,3-triazole by aid of aldehyde and sodium bisulfite adduct
The invention relates to a method for preparing 4-aryl-NH-1,2,3-triazole by the aid of aldehyde and sodium bisulfite adduct. The method is characterized by comprising steps as follows: the aldehyde and sodium bisulfite adduct, a nitrocompound, sodium azide, a solvent and an additive react at the temperature of 60-150 DEG C for 1-10 h with a one-pot method, after the reaction ends, aftertreament is performed, and 4-aryl-NH-1,2,3-triazole can be prepared. The cheap and easy-to-obtain aldehyde and sodium bisulfite adduct, nitrocompound and sodium azide are taken as raw materials, and 4-aryl-NH-1,2,3-triazole compounds can be conveniently prepared from the three components. Compared with existing methods, the method has the advantages that the raw materials are low in cost and simple and easy to obtain, the operation is convenient, and the reaction efficiency is high.
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Paragraph 0024

(2017/01/02)

Synthetic method of NH-1,2,3-triazole bipyridine compounds
The invention relates to a novel synthetic method of NH-1,2,3-triazole bipyridine compounds. According to the methods, pyridinecarboxaldehyde, nitroalkane, sodium azide and a catalyst are sequentially added to a reaction solvent in a reaction container, the materials are stirred in the air under a heating condition and react, and the NH-1,2,3-triazole bipyridine compounds are prepared. The method has the benefits as follows: cheap and available AlCl3 is taken as the catalyst, aromatic aldehyde, nitroalkane and sodium azide have a one-pot reaction, the reaction conditions are mild, the yield is high, the raw materials are available, and the NH-1,2,3-triazole bipyridine compounds are synthesized conveniently and effectively.
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Paragraph 0024; 0025; 0026; 0027; 0028; 0029

(2016/10/10)

Copper-catalyzed synthesis of 4-Aryl-1H-1,2,3-triazoles from 1,1-dibromoalkenes and sodium azide
A new methodology for the Cu-catalyzed synthesis of 1H-1,2,3-triazoles from 1,1-dibromoalkenes and sodium azide is presented. Aryl dibromoolefins were efficiently converted into the corresponding 1,2,3-triazoles. A comprehensive number of functional group
Wang, Xiaokun,Kuang, Chunxiang,Yang, Qing
experimental part
p. 424 - 428
(2012/02/03)

Identification of a sirtuin 3 inhibitor that displays selectivity over sirtuin 1 and 2
As part of an effort to identify novel selective modulators of sirtuins, we synthesized and tested several isosteres and constrained analogues of nicotinamide. Biological data suggest that compound 2 is selective for Sirt3 over Sirt1 and Sirt2.
Galli, Ubaldina,Mesenzani, Ornella,Coppo, Camilla,Sorba, Giovanni,Canonico, Pier Luigi,Tron, Gian Cesare,Genazzani, Armando A.
p. 58 - 66,9
(2020/07/31)

Rational design of 4-aryl-1,2,3-triazoles for indoleamine 2,3-dioxygenase 1 inhibition
Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target for the treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used computational structure-based methods to design more potent ligands. This approach yielded highly efficient low molecular weight inhibitors, the most active being of nanomolar potency both in an enzymatic and in a cellular assay, while showing no cellular toxicity and a high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.
R?hrig, Ute F.,Majjigapu, Somi Reddy,Grosdidier, Aurélien,Bron, Sylvian,Stroobant, Vincent,Pilotte, Luc,Colau, Didier,Vogel, Pierre,Van Den Eynde, Beno?t J.,Zoete, Vincent,Michielin, Olivier
experimental part
p. 5270 - 5290
(2012/08/28)

Highly N2-selective palladium-catalyzed arylation of 1,2,3-triazoles
A familiar ring? Highly N2-selective arylation of 4,5-unsubstituted and 4-substituted 1,2,3-triazoles was achieved for the first time by the Pd/1 catalyst system. A wide range of N2-aryl-1,2,3- triazoles were prepared from aryl bromi
Ueda, Satoshi,Su, Mingjuan,Buchwald, Stephen L.
supporting information; experimental part
p. 8944 - 8947
(2011/10/19)

Copper(I) iodide-catalyzed synthesis of 4-aryl-1 H -1,2,3-triazoles from anti -3-aryl-2,3-dibromopropanoic acids and sodium azide
4-Aryl-1H-1,2,3-triazoles were synthesized from anti-3-aryl-2,3- dibromopropanoic acids and sodium azide by using inexpensive copper(I) iodide as the catalyst in dimethyl sulfoxide
Jiang, Yubo,Kuang, Chunxiang,Yang, Qing
experimental part
p. 4256 - 4260
(2011/02/25)

Bromo-directed N-2 alkylation of NH-1,2,3-triazoles: Efficient synthesis of poly-substituted 1,2,3-triazoles
"Chemical Equation Presented" Reaction of 4-bromo-NH-1,2,3- triazoles 2 with alkyl halides In the presence of K2CO3 in DMF produced the corresponding 2-substituted 4-bromo1,2,3-triazoles 5 In a regioselective process. Subsequent Suzuki cross-coupling reaction of these bromides provided an efficient synthesis of 2,4,5-trisubstituted triazoles 3. In addition, reduction of the bromotriazoles by hydrogenation furnished an efficient synthesis of 2,4-disubstituted triazoles 8.
Wang, Xiao-Jun,Sidhu, Kanwar,Zhang, Li,Campbell, Scot,Haddad, Nizar,Reeves, Diana C.,Krishnamurthy, Dhileepkumar,Senanayake, Chris H.
scheme or table
p. 5490 - 5493
(2010/02/28)

Compounds and methods
Compounds of this invention are non-peptide, reversible inhibitors of type 2 methionine aminopeptidase, useful in treating conditions mediated by angiogenesis, such as cancer, haemangioma, proliferative retinophathy, rheumatoid arthritis, atherosclerotic
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(2008/06/13)

Bioisosteres of arecoline: 1,2,3,6-Tetrahydro-5-pyridyl-substituted and 3- piperidyl-substituted derivatives of tetrazoles and 1,2,3-triazoles. Synthesis and muscarinic activity
A series of arecoline bioisosteres, where the ester group is replaced by a 1,2,3-triazol-4-yl or a tetrazol-5-yl group, was synthesized and evaluated in vitro for affinity and efficacy at muscarinic receptors and in vivo for cholinergic side effects. The corresponding piperidine derivatives were also studied. In the 1,2,3,6-tetrahydropyridyl-1,2,3-triazole series, only derivatives with 2-substituents in the 1,2,3-triazole ring exert muscarinic agonist activity. The same trend is seen in the corresponding tetrazole series, where only 2-substituted derivatives display muscarinic agonist activity. The methyl derivatives in both series are full agonists, whereas the derivatives with longer side chains are partial agonists. Introduction of methyl substituents in the 1,2,3,6-tetrahydropyridine ring generally lowers affinity considerably except for the 3-substituted derivatives, where some activity is retained. In both the 1,2,3-triazole and tetrazole series, derivatives without substituents at the basic nitrogen in the 1,2,3,6- tetrahydropyridine ring are unselective full agonists, whereas the methyl- substituted derivatives generally are more M1 selective compared to M2. Larger substituents than methyl abolish activity. The 4-(3-piperidyl)-1,2,3- triazole and 5-(3-piperidyl)-2H-tetrazole derivatives are generally less active than the corresponding 1,2,3,6-tetrahydropyridine derivatives, and only the 2-allyl- and 2-propargyl-1,2,3-triazole derivatives display activities comparable to the most active compounds in the 1,2,3,6- tetrahydropyridine series. The propargyl derivative is an unselective full agonist, and resolution did not reveal any stereoselectivity. The allyl derivative is a partial agonist with some selectivity for the M1 receptor, and testing of the enantiomers showed that the (+)-enantiomer is an unselective partial agonist, whereas the (-)-enantiomer is a partial agonist with preference for the M1 receptor. Generally, the structure-activity relationships of the 1,2,3-triazole and tetrazole series are very similar, and two compounds, 2-ethyl-4-(1-methyl-1,2,3,6-tetrahydro-5-pyridyl)-1,2,3- triazole and 2-ethyl-5-(1-methyl-l,2,3,6-tetrahydro-5-pyridyl)-2H-tetrazole, are M1 agonists/M2 antagonists. Muscarinic compounds with this profile are of particular interest as drugs for the treatment of Alzheimer's disease.
Moltzen,Pedersen,Bogeso,Meier,Frederiksen,Sanchez,Lembol
p. 4085 - 4099
(2007/10/02)

1,2,3-Triazole and tetrazole substituted piperidine or tetrahydropyridine compounds useful as acetylcholine agonists
The present invention relates to novel compounds of the following formula, where the dotted line designates an optional bond: STR1 wherein "het" designates a five membered heterocyclic ring which may include 1 or 2 double bonds and 1-4 heteroatoms selected from nitrogen, oxygen or sulphur, provided that "het" may not designate a 1,2,4- or 1,3,4-oxadiazole; R1 is selected from hydrogen, lower alkyl, optionally substituted with phenyl which may be substituted with halogen, lower alkyl, or lower alkoxy, or a group R6 --CO--NH--CH2 -- or R6 --O--CO--, wherein R6 is lower alkyl, branched or unbranched, or phenyl optionally substituted with halogen, trifluoromethyl, lower alkyl, hydroxy, lower alkoxy, or lower acyloxy; R2 and R3 are the same or different, each representing hydrogen, lower alkyl, cycloalkyl (3-6 C-atoms), lower alkenyl, lower alkadienyl, lower alkynyl, optionally substituted with hydroxy, halogen or phenyl, in which the phenyl group may be substituted with halogen, trifluoromethyl, lower alkyl, hydroxy or lower alkoxy; R2 and R3 may further, respectively, be selected from trifluoromethyl or phenyl optionally substituted with halogen, trifluoromethyl, lower alkyl, hydroxy, lower alkoxy or lower acyloxy, or R2 and R3 may, respectively, be a group OR7 or SR7 wherein R7 is defined as R2 or R3, and if "het" includes 2 or more carbon atoms, R4 and R5 are the same or different, and each is defined as R2 or R3, and if "het" includes only one carbon atom, there is only one substituent, R4, on the heterocyclic ring, and R4 is defined as R2 or R3, as well as individual stereo isomers and pharmaceutically acceptable acid addition salts thereof. The invention moreover relates to methods for the preparation of the compounds of formula I, to novel intermediates, to pharmaceutical compositions containing same and to methods for the treatment of disorders, caused by malfunction of the acetylcholine (AcCh) or muscarinic system, by administering a non-toxic effective amount of a compound of formula I.
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(2008/06/13)

Chemical Properties

Melting Point: 180-182 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7))
Boiling Point: 386.6±17.0 °C(Predicted)
Density: 1.296±0.06 g/cm3(Predicted)
Storage Temp.:2-8°C
PKA: 7.54±0.70(Predicted)
PSA: 54.46000
LogP: 0.86670

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Chemical Properties

Melting Point: 180-182 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7))

Boiling Point: 386.6±17.0 °C(Predicted)

Density: 1.296±0.06 g/cm3(Predicted)

Storage Temp.:2-8°C

PKA: 7.54±0.70(Predicted)

PSA: 54.46000

LogP: 0.86670

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