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135-67-1Relevant articles and documents
Microwave assisted rapid synthesis of phenoxazines and benzopyridoxazines
Anchan, Kavitha,Puttappa, Nagaswarupa H.,Poongavanam, Baburajan,Sarkar, Sujit Kumar
, p. 635 - 646 (2020/11/27)
A facile protocol for the synthesis of phenoxazines and benzopyridoxazines by Smiles rearrangement have been demonstrated in short reaction time under microwave irradiation. The control experiments suggest that a reaction proceeds through Smiles rearrangement followed SNAr ring closure by in situ cascade process. In our present work, both the electron donating and electron withdrawing groups were tolerant and provided a corresponding phenoxazine/benzopyridoxazine in good to moderate yields.
Combined KOH/BEt3Catalyst for Selective Deaminative Hydroboration of Aromatic Carboxamides for Construction of Luminophores
Li, Jinshan,Wang, Jiali,Yang, Jianguo,Yao, Wubing,Zhong, Aiguo
, p. 8086 - 8090 (2020/11/03)
The selective catalytic C-N bond cleavage of amides into value-added amine products is a desirable but challenging transformation. Molecules containing iminodibenzyl motifs are prevalent in pharmaceutical molecules and functional materials. Here we established a combined KOH/BEt3 catalyst for deaminative hydroboration of acyl-iminodibenzyl derivatives, including nonheterocyclic carboxamides, to the corresponding amines. This novel transition-metal-free methodology was also applied to the construction of Clomipramine and luminophores.
Hydride-catalyzed selectively reductive cleavage of unactivated tertiary amides using hydrosilane
Yao, Wubing,Li, Rongrong,Yang, Jianguo,Hao, Feiyue
, p. 3874 - 3878 (2019/08/07)
The first hydride-catalyzed reductive cleavage of various unactivated tertiary amides, including the biologically active aryl-phenazine carboxamides and the challenging non-heterocyclic carbonyl functions, using low-cost hydrosilane as a reducing reagent has been developed. The novel catalyst system exhibits high efficiency and exclusive selectivity, providing the desired amines in useful to excellent yields under mild conditions. Overall, this transition metal-free process may offer a versatile alternative to currently employed expensive reducing reagents, high-pressure hydrogen or metal systems for the selective reductive cleavage of amides.
A disubstituted amide derivatives decarbonylation hydrogenation green new method (by machine translation)
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Paragraph 0054; 0055; 0056; 0057, (2018/02/04)
The invention relates to a high efficiency, high selectivity of the disubstituted amide derivatives of decarbonylation hydrogenation reaction green new method. For the first time to the metallic compound triethylborane as catalyst, under mild conditions can be conveniently catalytic N, N - di-aryl substituted amide and its derivative and cheap and easy to obtain organic silicon reagent selective preparation of secondary organic amine product. Compared with the traditional method, the new method generally has the wide substrate universality, functional group compatibility outstanding, simple operation and the like. For the first time in order to realize the organic silicon reagent as reducing agent and amide compounds decarbonylation hydrogenation reaction, is the reduction of amides and derivatives thereof, in particular the organic light-emitting diodes (OLEDs) material unit - diaryl amine compound of the laboratory preparation or industrial production provides a brand-new "green" response strategies. (by machine translation)
Characterization of HJ-PI01 as a novel Pim-2 inhibitor that induces apoptosis and autophagic cell death in triple-negative human breast cancer
Zhao, Yu-Qian,Yin, Yi-Qiong,Liu, Jie,Wang, Gui-Hua,Huang, Jian,Zhu, Ling-Juan,Wang, Jin-Hui
, p. 1237 - 1250 (2016/09/09)
Aim: Pim-2 is a short-lived serine/threonine kinase, which plays a key role in metastasis of breast cancer through persistent activation of STAT3. Although the crystal structure of Pim-2 has been reported, but thus far no specific Pim-2-targeted compounds have been reported. In this study, we identified a novel Pim-2 inhibitor, HJ-PI01, by in silico analysis and experimental validation. Methods: The protein-protein interaction (PPI) network, chemical synthesis, molecular docking, and molecular dynamics (MD) simulations were used to design and discover the new Pim-2 inhibitor HJ-PI01. The anti-tumor effects of HJ-PI01 were evaluated in human breast MDA-MB-231, MDA-MB-468, MDA-MB-436, MCF-7 cells in vitro and in MDA-MB-231 xenograft mice, which were treated with HJ-PI01 (40 mg·kg-1 ·d-1, ig) with or without lienal polypeptide (50 mg·kg-1 ·d-1, ip) for 10 d. The apoptosis/autophage-inducing mechanisms of HJ-PI01 were elucidated using Western blots, immunoblots, flow cytometry, transmission electron microscopy and fluorescence microscopy. Results: Based on the PrePPI network, the potential partners interacting with Pim-2 in regulating apoptosis (160 protein pairs) and autophagy (47 protein pairs) were identified. Based on the structural characteristics of Pim-2, a total of 15 compounds (HJ-PI01 to HJ-P015) were synthesized, which showed moderate or remarkable anti-proliferative potency in the human breast cancer cell lines tested. The most effective compound HJ-PI01 exerted a robust inhibition on MDA-MB-231 cells compared with chlorpromazine and the pan-Pim inhibitor PI003. Molecular dynamics (MD) simulation revealed that HJ-PI01 had a good binding score with Pim-2. Moreover, HJ-PI01 (300 nmol/L) induced death receptor-dependent and mitochondrial apoptosis as well as autophagic death in MDA-MB-231 cells. In MDA-MB-231 xenograft mice, administration of HJ-PI01 remarkably inhibited the tumor growth and induced tumor cell apoptosis in vivo. Co-administration of HJ-PI01 with lienal polypeptide could improve the anti-tumor activity of HJ-PI01 and reduce its toxicity. Conclusion: The newly synthesized compound, HJ-PI01, can induce death receptor/mitochondrial apoptosis and autophagic cell death by targeting Pim-2 in human breast cancer cells in vitro and in vivo.
Transition-metal-free intramolecular N-arylations
Thome, Isabelle,Bolm, Carsten
scheme or table, p. 1892 - 1895 (2012/05/20)
N-Substituted phenoxazines and related aza analogs have been prepared from N-acetylated aryloxy anilides by transition-metal-free, base-catalyzed cyclization reactions. In the presence of a mixture of 10 mol % of N,N′-dimethylethylenediamine (DMEDA) and 2 equiv of K2CO 3 in toluene at 135 °C the products are obtained in high yields.
NOVEL AROMATIC COMPOUND AND POLYARYLENE COPOLYMER HAVING NITROGEN-CONTAINING HETEROCYCLE INCLUDING SULFONIC ACID GROUP IN SIDE CHAIN
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, (2010/06/22)
Provided is a solid polymer electrolyte having increased heat resistance and high proton conductivity and a proton conductive membrane composed of the electrolyte. Also provided is a copolymer having a sulfonic acid group. The copolymer includes a repeating unit represented by Formula (1): (in the formula, Y denotes at least one kind of structure selected from the group consisting of —CO—, —SO2—, —SO—, —CONH—, —COO—, —(CF2)l— (l is an integer of 1 to 10), and —C(CF3)2—; W denotes at least one kind of structure selected from the group consisting of a direct bond, —CO—, —SO2—, —SO—, —CONH—, —COO—, —(CF2)l— (l is an integer of 1 to 10), —C(CF3)2—, —O—, and —S—; Z denotes a direct bond or at least one kind of structure selected from the group consisting of —(CH2)l—(l is an integer of 1 to 10), —C(CH3)2—, —O—, —S—, —CO—, and —SO2—; R30 denotes a nitrogen-containing aromatic ring having a substituent represented by —SO3H, —O(CH2)hSO3H, or —O(CF2)hSO3H (h is an integer of 1 to 12); p is an integer of 0 to 10; q is an integer of 0 to 10; r is an integer of 1 to 5; and k is an integer of 0 to 4).
Heterocyclization of N-propenyl-substituted phenothiazines and phenoxazines using electrophiles in an anhydrous medium
Sirotkina,Khlebnikov,Napilkova
experimental part, p. 1505 - 1509 (2009/07/04)
10-Propenylphenothiazine reacts with a catalytic amount of BF 3·Et2O in dry ethyl acetate via intramolecular heterocyclization of an intermediate dimeric cation to give mainly 1-ethyl-2-methyl-3-(phenothiazin-10-yl)-2,3-dihydro-1H-pyrido[3,2,1-k,l] phenothiazine and a minor product through fission of phenothiazine which is 1-ethyl-2-methyl-1H-pyrido[3,2,1-k,l]phenothiazine. Under similar conditions 10-propenylphenoxazine gave an oligomer (degree of polymerization 4.4) and the minor product 1-ethyl-2-methyl-1H-pyrido[3,2,1-k,l]phenoxazine likely formed similarly to the phenothiazine analog from the corresponding product of intramolecular heterocyclization (the latter not being observed in the reaction mixture).
Substituted quinobenzoxazine analogs
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, (2008/06/13)
The present invention relates to quinobenzoxazines analogs having the general formula: and pharmaceutically acceptable salts, esters and prodrugs thereof; wherein A, U, V, W, X and Z are substituents. The present invention also relates to methods for using such compounds.
Novel derivatives and analogues of galanthamin
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, (2008/06/13)
New compounds of general formula I 1
