- Compound of dipyrrolopyridine structure Preparation method and medical application
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The invention discloses a compound with a dipyrrolo-pyridine structure as well as a preparation method and medical application thereof. The compound provided by the invention has obvious inhibitory activity on JAK family proteins, is an effective JAK inhibitor, and has the prospect of being developed into drugs for inhibiting JAK and further treating diseases.
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Paragraph 0228-0231
(2021/08/25)
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- One-pot, two-step synthesis of 7-methylene-1,5-piperazine-fused 1,2,3-triazoles
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A facile, one-pot two-step synthesis of 7-methylene-1,5-piperazine-fused 1,2,3-triazole derivatives has been developed. The protocol employs an N-allylation of N-propargylated amines with 2,3-dibromopropene in the presence of K2CO3 in DMSO and a CuI-catalyzed [3 + 2] cycloaddition reaction of the synthetic N-(2-bromoallyl)-N-propargyl amines with sodium azide sequentially. Such a method provides methylene-substituted 1,2,3-triazole fused piperazines with some advantages such as simple operation, high efficiency and good product yield (80–91%) through readily available starting materials.
- Kuang, Lu,Ming, Peng,Wan, Chang-Feng,Chen, Jun-Min,Sheng, Shou-Ri
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p. 563 - 569
(2020/11/19)
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- Synthesis and biological evaluation of coumarin-linked 4-anilinomethyl-1,2,3-triazoles as potent inhibitors of carbonic anhydrases ix and xiii involved in tumorigenesis
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A series of coumarin-linked 4-anilinomethyl-1,2,3-triazoles (6a–t) was synthesized via a molecular hybridization approach, through carbon C-6 of the coumarin moiety. The synthesized compounds were evaluated for their inhibition of carbonic anhydrase (CA)
- Thacker, Pavitra S.,Tiwari, Prerna L.,Angeli, Andrea,Srikanth, Danaboina,Swain, Baijayantimala,Arifuddin, Mohammed,Supuran, Claudiu T.
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- Palladium-Catalyzed Allenamide Carbopalladation/Allylation with Active Methine Compounds
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A palladium-catalyzed allenamide carbopalladation/allylation with active methine compounds has been developed. Various indoles and isoquinolinones bearing a quaternary carbon center were achieved with good efficiency, a broad substrate scope and good functional group tolerance. This reaction underwent cascade oxidative addition, carbopalladation, and allylic alkylation, and two new C-C bonds were formed in one pot.
- Zhu, Xiaoyi,Li, Ruibo,Yao, Hequan,Lin, Aijun
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supporting information
p. 4630 - 4634
(2021/06/28)
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- New ursolic acid derivatives bearing 1,2,3-triazole moieties: design, synthesis and anti-inflammatory activity in vitro and in vivo
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Abstract: In order to discover novel anti-inflammatory agents, three series of compounds obtained by appending 1,2,3-triazole moieties on ursolic acid were designed and synthesized. All compounds have been screened for their anti-inflammatory activity by using an ear edema model. The potent anti-inflammatory compound was subjected to in vitro cyclooxygenase COX-1/COX-2 inhibition assays. In general, the derivatives were found to be potent anti-inflammatory activity. Especially, the compound 11b exhibited the strongest activity of all of the compounds prepared, with 82.81% inhibition after intraperitoneal administration, which was better than celecoxib as a positive control. Molecular docking results unclose the rationale for the interaction of the compound 11b with COX-2 enzyme. Further studies revealed that compound 11b exhibited effective COX-2 inhibitory activity, with half-maximal inhibitor concentration (IC50) value of 1.16?μM and selectivity index (SI = 64.66) value close to that of celecoxib (IC50 = 0.93?μM, SI = 65.47). Taken together, these results could suggest a promising chemotype for development of new COX-2-targeting anti-inflammatory agent. Graphic abstract: [Figure not available: see fulltext.]
- Bai, Xue-Qian,Cao, Li-Ting,Li, Chun-Shi,Sun, Si-Mei,Zhang, Tian-Yi,Zhao, Dong-Hai
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- Stereoselective Synthesis of Hexahydroimidazo[1,2- a]quinolines via SN2-Type Ring-Opening Hydroarylation-Hydroamination Cascade Cyclization of Activated Aziridines with N-Propargylanilines
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A novel synthetic approach for the construction of 1,2,3,3a,4,5-hexahydroimidazo[1,2-a]quinolines in good yields (up to 75%) with excellent stereoselectivity (dr up to 94:6, ee up to >99%) under one-pot domino ring-opening cyclization (DROC) conditions ha
- Bhattacharyya, Aditya,Chauhan, Navya,Ghorai, Manas K.,Pradhan, Sajan,Shahi, Chandan K.
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supporting information
p. 7903 - 7908
(2020/11/02)
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- Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N -propargylanilines with diverse carbon pronucleophiles: Facile access to functionalized tetrahydroquinolines
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Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N-propargylanilines with two types of carbon pronucleophiles (nitromethane as a sp3 carbon pronucleophile and phenylacetylenes as sp carbon pronucleophiles) proceeded to give the 2-substituted tetrahydroquinolines in good yields with 100percent atomic utilization without any additional external oxidants.
- Li, Guangzhe,Wang, Chengdong,Li, Yueqing,Shao, Kun,Yu, Guo,Wang, Shisheng,Guo, Xiuhan,Zhao, Weijie,Nakamura, Hiroyuki
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supporting information
p. 7333 - 7336
(2020/07/23)
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- Facile, catalyst-free cascade synthesis of sulfonyl guanidines: Via carbodiimide coupling with amines
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An expeditious catalyst-free cascade coupling of N,N-dibromoarylsulfonamides with isonitriles and amines via carbodiimide intermediates has been developed. The protocol represents an elegant pathway for sulfonyl guanidines at room temperature within a short time with high yields and wide substrate scope. The carbodiimide intermediate could also be isolated in an appreciable yield.
- Hazarika, Debojit,Borah, Arun Jyoti,Phukan, Prodeep
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supporting information
p. 1418 - 1421
(2019/02/05)
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- Synthesis and Activity of 1,2,3-Triazole Aminopyrimidines against Cyanobacteria as PDHc-E1 Competitive Inhibitors
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Cyanobacteria harmful algal blooms are of global concern, but all currently available algicides in the market are nonselective and have potential side effects on nontarget species. In the present work, two series of compounds (4 and 6) comprising 16 novel
- Zhou, Yuan,Feng, Jiangtao,Feng, Lingling,Xie, Dan,Peng, Hao,Cai, Meng,He, Hongwu
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p. 12538 - 12546
(2019/11/13)
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- Hypervalent iodine compound containing heterocyclic ring as well as preparation method and application thereof
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The invention discloses a hypervalent iodine compound containing a heterocyclic ring as well as a preparation method and application thereof. A structure of the compound is shown as a formula (I): theformula (I) is shown in the description, wherein R is selected from hydrogen, halogen, alkyl, alkoxy, halogenated alkyl, halogenated alkoxy, nitryl, cyano, hydroxyl or -COOR'; R' is alkyl or halogenated alkyl; and Het is substituted or non-substituted 1,4-benzopyranone, substituted or non-substituted quinolone, substituted or non-substituted isoquinoline, substituted or non-substituted thiobenzopyranone, substituted or non-substituted coumarin and substituted or non-substituted oxepin. The compound disclosed by the invention is novel in structure and is the hypervalent iodine compound containing the heterocyclic ring; the hypervalent iodine compound is stable in structure and simple in preparation method; and meanwhile, the hypervalent iodine compound has a very good inhibition effect onML-1 and MOLM-13 cells and has an extremely great application prospect on prevention and/or treatment effect on leukemia.
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Paragraph 0144; 0145; 0146
(2019/01/08)
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- One-pot preparation of pyrrole derivatives via the copper-catalyzed [4+1] annulation of propargylic amines with ethyl glyoxylate and phenylglyoxal in the presence of piperidine
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We describe how copper(II) chloride efficiently catalyzes the [4+1] annulation of propargylamines with either ethyl glyoxylate or phenylglyoxal functioning as a C1 unit, in the presence of piperidine, which leads to a straightforward and one-pot preparati
- Sakai, Norio,Suzuki, Hiroki,Hori, Hiroaki,Ogiwara, Yohei
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supporting information
p. 63 - 66
(2016/12/23)
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- Design, synthesis and antibacterial evaluation of novel 1,2,3-triazole derivatives incorporating 3′-deoxythymidine
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A series of novel 1,2,3-triazole derivatives incorporating 3′-deoxythymidine were designed, synthesised and characterised. Antibacterial activity against Escherichia coli and Staphylococcus aureus was evaluated for all of the synthesised compounds and com
- Mao, Long-Fei,Xu, Gui-Qing,Sun, Bin,Jiang, Yu-Qin,Dong, Wen-Pei,Zhang, Shu-Ting,Shen, Jia-Xuan,He, Xing
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p. 645 - 649
(2017/12/26)
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- Synthesis of 2-Indolyltetrahydroquinolines by Zinc(II)-Catalyzed Intramolecular Hydroarylation-Redox Cross-Dehydrogenative Coupling of N-Propargylanilines with Indoles
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An intramolecular hydroarylation-redox cross-dehydrogenative coupling (CDC) of propargylic anilines with indoles proceeded in the presence of zinc(II) catalysts to give 2-indolyltetrahydroquinolines in good to high yields. Three C-H bonds (two sp2and one sp3) are activated in one shot and these hydrogen atoms are trapped by a propargylic triple bond in the molecule.
- Li, Guangzhe,Nakamura, Hiroyuki
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supporting information
p. 6758 - 6761
(2016/06/09)
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- AgNO2 as the NO Source for the Synthesis of Substituted Pyrazole N-Oxides from N-Propargylamines
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A straightforward method for synthesizing the pyrazole N-oxides from N-propargylamines and AgNO2 through oxidation/cyclization reaction had been developed. AgNO2 was used as the NO source for the first time to synthesize pyrazole N-o
- Yuan, Bingxiang,Zhang, Fuming,Li, Zhuomei,Yang, Shenghua,Yan, Rulong
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supporting information
p. 5928 - 5931
(2016/11/29)
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- Copper(II)-Catalyzed [4+1] annulation of propargylamines with N,O-acetals: Entry to the synthesis of polysubstituted pyrrole derivatives
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Described herein is the CuCl2-catalyzed [4+1] annulation of a variety of propargylamines with N,O-acetals that function as a C1 unit, leading to the production of polysubstituted pyrrole derivatives. Three important features of the N,O-acetal during the [4+1] annulation series via 5-endo-dig cyclization are described: an enolizable substituent adjacent to the central sp3-carbon is required, the central sp3-carbon displays the functions of both an electrophile and a nucleophile, and liberation of the secondary amine smoothly leads to the aromatization. A CuCl2-catalyzed [4+1] annulation of propargylamines with N,O-acetals having an ester, a ketone, and an amide moiety, leading to the facile preparation of polysubstituted pyrrole derivatives is presented. This annulation series was achieved through 5-endo-dig cyclization and subsequent aromatization in one pot.
- Sakai, Norio,Hori, Hiroaki,Ogiwara, Yohei
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supporting information
p. 1905 - 1909
(2015/03/18)
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- 2-[N-Alkyl(R-phenyl)-aminomethyl]-3-phenyl-7-trifluoromethylquinoxalines as anticancer agents inhibitors of folate enzymes
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Based on our previous results on the ascertained potent growth inhibition effect against a panel of 60 human tumors cell lines at National Cancer Institute of Bethesda (NCI), we have synthesized a novel series of thirty-one 2-[N-methyl(R-phenyl)-aminomethyl]-3-phenyl-7-trifluoromethylquinoxalines (1-31). The lead compound 1 was previously reported to be endowed with significant inhibition against hDHFR enzyme, with a Ki of 0.2 μM. Docking studies were performed on compound 1 and here reported to predict its binding conformation to human dihydrofolate reductase (hDHFR). All compounds (1-31) were assayed versus hDHFR and human thymidylate synthase (hTS). From the screening emerged that all compounds inhibited hDHFR with Ki values included between 0.2 and 11 μM, while only a few (6, 21, 24, 27, 29) showed great activity and selectivity towards hTS. Evaluation of the anticancer activity was performed by NCI, first against the three cell line panel, and only the most active compounds (17, 21, 24, 26, 27) were evaluated on a panel of 60 human tumor cell lines. Compound 21 was the most active against all cell lines with log GI50 equal to -5.49 and log LC50 equal to -4.19 and maintained significant percent of growth inhibition on seven cancer cell lines at the concentration of 1 μM. Compound 17 was the second most active and moreover showed interesting selectivity against some cell lines (Lung cancer: A549/ATCC, Melanoma: UACC-257, Ovarian Cancer: ovcar-8 and Renal cancer: RXF 393) at all concentration examined (100-0.01 μM).
- Piras, Sandra,Carta, Antonio,Briguglio, Irene,Corona, Paola,Paglietti, Giuseppe,Luciani, Rosaria,Costi, Maria Paola,Ferrari, Stefania
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p. 169 - 183
(2014/03/21)
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- One-pot synthesis of N-aryl propargylamine from aromatic boronic acid, aqueous ammonia, and propargyl bromide under microwave-assisted conditions
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A facile, one-pot synthesis of N-aryl propargylamine from aromatic boronic acid, aqueous ammonia, and propargyl bromide has been achieved under microwave-assisted conditions. The reactions can be smoothly completed within a total 10 min through a two-step procedure, including copper-catalyzed coupling of aromatic boronic acids with aqueous ammonia and following propargylation by propargyl bromide.
- Jiang, Yu-Bo,Zhang, Wen-Sheng,Cheng, Hui-Ling,Liu, Yu-Qi,Yang, Rui
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p. 779 - 782
(2014/06/09)
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- A microwave-assisted three-component synthesis of arylaminomethyl ?acetylenes: A facile access to terminal alkynes
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A simple, rapid, one-pot synthesis of arylaminomethyl acetylenes is achieved under microwave-assisted conditions (power? =? 5 W) using aromatic boronic acids, aqueous ammonia, propargyl halides, copper(I) oxide and water as the solvent. The reactions are complete within ten minutes affording good to excellent yields of the products. Georg Thieme Verlag Stuttgart. New York.
- Jiang, Yubo,Huang, Shaojun
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supporting information
p. 407 - 410
(2014/03/21)
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- An expedient approach to substituted triazolo[1,5-a][1,4]benzodiazepines via Cu-catalyzed tandem Ullmann C-N coupling/azide-alkyne cycloaddition
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An approach to the synthesis of triazolo[1,5-a][1,4]benzodiazepines comprising copper catalyzed tandem Ullmann C-N coupling followed by azide-alkyne cycloaddition has been described. The reaction of o-azidobenzylbromide and N-propargylated aniline derivat
- Majumdar,Ganai, Sintu
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supporting information
p. 6192 - 6195
(2013/10/22)
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- Ag-containing all-carbon 1,3-dipoles: Generation and formal cycloaddition for furo[3,2-b]-β/γ-lactams
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A new strategy for highly diastereoselective synthesis of furo[3,2-b]-β-lactams and furo[3,2-b]-γ-lactams via a novel Ag(i)-mediated intramolecular 1,3-dipolar cycloaddition of oxo-N- propargylamides, is developed and the possible mechanism of these trans
- Zhang, Zhiguo,Zhang, Qian,Ni, Zhikun,Liu, Qun
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body text
p. 1269 - 1271
(2010/07/05)
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- Efficient preparation of novel N-propargylic β-enaminones from the reaction of β-alkoxyvinyltrihalomethyl[carboxy]ketones and propargylamines
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Fifteen N-propargylic β-enaminones were synthesized from the reaction of propargyl amines [4-X-PhNHCH2C=CH, where X = H, Me] and 4-alkoxy-1,1,1-trihalo[ethoxy]-3-alken-2-ones [RC(O)CH=C(R1)OMe, where R = CF3, CCl3/su
- Martins, Marcos A.P.,Rossatto, Marcelo,Prola, Lizie D.T.,Moreira, Dayse N.,Campos, Patrick T.,Zanatta, Nilo,Bonacorso, Helio G.
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experimental part
p. 12 - 18
(2010/10/19)
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- Preparation and cyclization of some N-(2,2-Dimethylpropargyl) homo- And heteroaromatic amines and the synthesis of some pyrido[2,3-d]pyrimidines
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The Cu(I) catalyzed cyclization of o-substituted N-(2,2-dimethylpropargyl) anilines yields 8-substituted 2,2-dimethyl-1,2-dihydroquinolines, while m-substituted analogues provide a mixture of 5- and 7-substituted dihydroquinoline systems. This reaction can be extended to 2-amino-N-(2,2- dimethylpropargyl)anthracene, yielding a dihydronaphtho[2,3-f]quinoline product, and to aminoquinoline derivatives, which yield substituted phenanthroline products. Pyridine analogues did not cyclize, apparently because of complexation with the copper reagent. An alternative synthetic approach to these cyclized products, when complexation may be a problem, is illustrated by the following example. 2-Chloro-4-N-(2,2-dimethylpropargyl)pyrimidine was reduced using a Lindlar catalyst to the corresponding alkene which did not undergo an amino-Claisen rearrangement. However, the 5-bromopyrimidine alkene analogue underwent addition with phenylselanyl bromide to give a product that cyclized, using butyllithium, to a pyrido[2,3-d]pyrimidine selenium-containing product from which the selenium moiety could be removed to yield either a dihydro- or a tetrahydro-pyrido[2,3-d]pyrimidine system. A Heck reaction on the 5-bromopyrimidine alkene gave a 5-methylene-6,7-dihydro-5H-pyrrolo[2,3-d] pyrimidine. CSIRO 2005.
- Holman, Michelle A.,Williamson, Natalie M.,Ward, A. David
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p. 368 - 374
(2007/10/03)
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- Direct and selective N-monoalkynylation and N-monoalkenylation of anilines with alky(e)nyl methanesulfonates using methylmagnesium bromide as a base
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Several anilines were directly N-monoalkynylated and N-monoalkenylated with alkynyl methanesulfonates and alkenyl methanesulfonates, respectively, using methylmagnesium bromide as a base in good yields with high selectivities.
- Yoshida, Yoshihiro,Tanabe, Yoo
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p. 533 - 535
(2007/10/03)
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- Intramolecular aromatic substitution and amino-claisen rearrangement in substituted N-(2-propynyl)anilines on electron impact
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N-(2-Propynyl)anilines undergo amino-Claisen rearrangement to a minor extent in the ion source, losing a molecule of HCN under electron impact conditions. However, metastable molecular ions with energies closer to threshold undergo Claisen rearrangement g
- Ramana,Sudha
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p. 1028 - 1033
(2007/10/03)
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- INFLUENCE OF THE NATURE OF THE LEAVING GROUP ON THE RATES OF THE REACTIONS OF ALKYNYL HALIDES AND ALKYNYL SULFONATES WITH PRIMARY ARYLAMINES IN ACETONITRILE
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For aminolysis reactions we have determined and quantitatively asessed the nonadditivity of the joint influence of the electronic effects of the substituents and the nature of the leaving group in alkynyl halide-alkynyl sulfonate-arylamine systems.
- Vizgert, R. V.,Korostylev, A. P.,Kru'tko, I. N.,Zen'kova, S. E.,Yakusheva, I. G.
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p. 120 - 124
(2007/10/02)
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- MUTUAL EFFECT OF STRUCTURE AND TEMPERATURE IN THE REACTIONS OF PROPARGYL BROMIDE WITH PRIMARY ARYLAMINES IN ACETONITRILE
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For the reactions of propargyl bromide with arylamines at various temperatures there is a direct relationship between the reactivity and the sensitivity to the structure of the arylamines and to temperature.The dependance of the correlation parameters on
- Vizgert, R. V.,Korostylev, A. P.,Krut'ko, I. N.,Zenkova, S. E.
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p. 1018 - 1021
(2007/10/02)
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- 3-PHENOXY-2-PHENYLSULPHINYLPROP-1-ENE AND 3-BROMO-2-PHENYLSULPHINYLPROP-1-ENE, SYNTHONS FOR N-ALKYLATED CYCLIC ENAMIDES.
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2-Alkyl(and aryl)amino-2-phenylsulphinylprop-1-enes (derived from benzylamine, cyclohexylamine, and p-toluidine), underwent conjugate addition with diethyl sodiomalonate to give adducts which cyclised to give N-alkylated lactams.Thermolysis of the lactams results in regioselective elimination of benzenesulphenic acid to give N-alkylated cyclic enamides in good yields.The 3-alkyl(and aryl)amino-2-phenylsulphinylprop-1-enes were conveniently prepared by the addition of benzenesulphenic acid to 3-alkyl(and aryl)aminoprop-1-ynes, and by reaction of 3-bromo- and 3-phenoxy-2-phenylsulphinylprop-1-ene with the appropriate amine.
- Khan, M. Akram,Al-Saleh, Balkis
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p. 320 - 333
(2007/10/02)
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- SELECTIVE SYNTHESIS OF MONO- AND DIPROPARGYLARYLAMINES ON ALUMINUM OXIDE
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Propargylarylamines are formed with preparative yields in the reaction of propargyl bromide with arylamines in a molar ratio of 1:3 on aluminum oxide.The use of aluminum oxide modified with potassium carbonate and a reduction in the relative amount of the
- Abdulganeeva, S. A.,Erzhanov, K. B.
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p. 466 - 469
(2007/10/02)
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