- Synthesis of phenazine-2,8-dicarboxylates
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Phenazine is a tricyclic heteroarene that forms the core of diverse functional molecules including DNA intercalators. However, 2,8-disubstituted phenazines are rare, and this potentially limits the medicinal development of this class of heterocycles. Here we describe the synthesis of two new members of this compound class (i.e. dimethyl phenazine-2,8-dicarboxylate and the corresponding diacid), following a synthetic route that involved inter- and intramolecular Buchwald-Hartwig N-arylations. We also detail a simple NMR-based method for proving the 2,8-disubstitution pattern, in order to counterbalance suspected structural misassignments elsewhere in the peer-reviewed and patent literature.
- Bhadbhade, Mohan M.,Constable, Grace E. O.,Hunter, Luke,Jung, Jane,Read, Roger W.,Wakelin, Laurence P. G.
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supporting information
(2022/01/12)
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- Synthesis and biological evaluation of an antibacterial azaborine retinoid isostere
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Our continued synthetic interest in this class of retinoids, CD437 and its analogs, against methicillin-resistant Staphylococcus aureus (MRSA) has brought us to explore further isosteric substitutions within the scaffold. Although our previous findings ha
- Haney, Brittney A.,Schrank, Cassandra L.,Wuest, William M.
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- A Practical Procedure for Regioselective Bromination of Anilines
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A highly practical procedure for the preparation of bromoanilines by using copper-catalyzed oxidative bromination has been developed. Treatment of free anilines with readily available NaBr and Na 2S 2O 8in the presence of a catalytic amount of CuSO 4·5H 2O enabled regioselective bromination.
- Takahashi, Yusuke,Seki, Masahiko
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p. 1828 - 1832
(2021/04/15)
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- METHOD FOR PRODUCING AROMATIC HALOGEN DERIVATIVE
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PROBLEM TO BE SOLVED: To provide a highly efficient and economically advantageous method for producing a halogen compound. SOLUTION: The method produces a halogen compound represented by formula (2) (X is a halogen atom, and b is an integer of 1-5) by reacting an aniline derivative represented by formula (1) (R1 is an ester group, a carbonyl group, a nitrile group, a nitro group, an optionally substituted alkyl group or an optionally substituted aralkyl group, and a is an integer of 0-4) with a halogenating agent in the presence of a copper catalyst and a persulfate. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0153-0156
(2020/07/28)
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- NEW CLASS OF DNA GYRASE AND/OR TOPOISOMERASE IV INHIBITORS WITH ACTIVITY AGAINST GRAM-POSITIVE AND GRAM-NEGATIVE BACTERIA
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The present invention relates to compounds having a structure of general formula (I), processes for their preparation, pharmaceutical compositions containing them as the active ingredient, to their use as medicaments and to their use in the manufacture of medicaments for use in the treatment of bacterial infections in humans and warm-blooded animals.
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Page/Page column 102
(2020/03/29)
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- Cu-mediated selective bromination of aniline derivatives and preliminary mechanism study
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A simple and efficient bromination of aniline, aniline derivatives, and analogs have been developed. Forty three examples were given and the highest yield reached was 98%. Different substrates including substituted aniline, pyridin-amine, N-substituted aniline, N,N-disubstituted aniline, N-phenyl-amide, N-phenyl-sulfonamide, and nitrogen-containing heterocycles were all reactive and selectively generated desired bromo-products. The method can be applied to synthesize drug intermediate and quinoxaline derivatives.
- Zhao, Hong-Yi,Yang, Xue-Yan,Lei, Hao,Xin, Minhang,Zhang, San-Qi
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supporting information
p. 1406 - 1415
(2019/05/01)
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- Direct Synthesis of Structurally Divergent Indole Alkaloids from Simple Chemicals
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A direct and structurally divergent synthesis of indole alkaloids from very simple 2-vinylanilines, alkynes and TBN via a novel substrate fragmentation/cycloaddition strategy has been developed, which provides an efficient noble-metal-free approach to access a library of highly valuable indole derivatives of tryptamines and tryptamine-related oximes, lactams, and lactones, as well as β-carbolines, spiroindolines, and hexa-hydropyrrolo[2,3-b]indoles.
- Shen, Tao,Zhu, Bencong,Lin, Fengguirong,Pan, Jun,Wei, Jialiang,Luo, Xiao,Liu, Jianzhong,Jiao, Ning
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supporting information
p. 815 - 818
(2018/07/31)
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- Direct Tryptophols Synthesis from 2-Vinylanilines and Alkynes via C - C Triple Bond Cleavage and Dioxygen Activation
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An unexpected metal-free C - C triple bond cleavage, dioxygen activation, and reassembly into tryptophol derivatives has been developed. This chemistry provides a novel, simple, and efficient approach to highly valuable tryptophol derivatives from simple substrates under mild conditions. The mechanistic studies may promote the discovery of new methodologies through C-C bond cleavage and dioxygen activation.
- Shen, Tao,Zhang, Yiqun,Liang, Yu-Feng,Jiao, Ning
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supporting information
p. 13147 - 13150
(2016/10/24)
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- Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization
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An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.
- Song, Song,Sun, Xiang,Li, Xinwei,Yuan, Yizhi,Jiao, Ning
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supporting information
p. 2886 - 2889
(2015/06/30)
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- Palladium-catalyzed carbonylative synthesis of benzoxazinones from N -(o -bromoaryl)amides using paraformaldehyde as the carbonyl source
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Carbonylation reactions have been widely used in organic synthesis. However, the manipulation of toxic and pressurized carbon monoxide limited their applications in organic laboratories. The search for alternative carbonyl sources as an important method for carbonylative organic synthesis is spreading. Herein, a series of substituted benzoxazinones were synthesized from N-(o-bromoaryl)amides by palladium-catalyzed carbonylation with paraformaldehyde as the carbonyl source, which is inexpensive, stable, and easy to use. Notably, this is the first example of using paraformaldehyde as the CO source in palladium-catalyzed carbonylative synthesis of heterocycles.
- Li, Wanfang,Wu, Xiao-Feng
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p. 10410 - 10416
(2015/02/19)
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- Fast and efficient bromination of aromatic compounds with ammonium bromide and Oxone
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A highly efficient, rapid and regioselective protocol was developed for the ring bromination of aromatic compounds under mild conditions with ammonium bromide as a source of bromine source and Oxone (potassium peroxysulfate) as an oxidant. No metal catalyst or acidic additive is required. A variety of aromatic compounds, including methoxy, hydroxy, amino, and alkyl arenes, reacted smoothly to give the corresponding monobrominated products in good to excellent yields in very short reaction times. Moreover, dibromination of deactivated anilines to give the corresponding dibromides proceeded in high yields. Interestingly, 1-(2-naphthyl)ethanone provided a ring-brominated product. Georg Thieme Verlag Stuttgart . New York.
- Naresh, Mameda,Arun Kumar, Macharla,Mahender Reddy, Marri,Swamy, Peraka,Nanubolu, Jagadeesh Babu,Narender, Nama
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p. 1497 - 1504
(2013/06/27)
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- Design and synthesis of a novel class of CK2 inhibitors: Application of copper- and gold-catalysed cascade reactions for fused nitrogen heterocycles
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Two classes of fused nitrogen heterocycles were designed as CK2 inhibitor candidates on the basis of previous structure-activity relationship (SAR) studies. Various dipyrrolo[3,2-b:2′,3′-e]pyridine and benzo[g]indazole derivatives were prepared using transition-metal-catalysed cascade and/or multicomponent reactions. Biological evaluation of these candidates revealed that benzo[g]indazole is a promising scaffold for potent CK2 inhibitors. The inhibitory activities on cell proliferation of these potent CK2 inhibitors are also presented.
- Suzuki, Yamato,Oishi, Shinya,Takei, Yoshinori,Yasue, Misato,Misu, Ryosuke,Naoe, Saori,Hou, Zengye,Kure, Tatsuhide,Nakanishi, Isao,Ohno, Hiroaki,Hirasawa, Akira,Tsujimoto, Gozoh,Fujii, Nobutaka
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experimental part
p. 4907 - 4915
(2012/08/08)
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- Synthesis and biological evaluation of a novel human stem/progenitor cells proliferation activator: 4-(4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl) thiosemicarbazide (Stemazole)
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Stem/progenitor cells are crucial for cell-based therapy and regenerative medicine, and their application in clinical and basic research requires a large supply of cells. To identify effective stem/progenitor cell proliferation activators, we synthesised a series of new 4-(4-(5-mercapto-1,3,4-oxadiazol-2- yl)phenyl) thiosemicarbazide (named Stemazole) derivatives. Preliminary evaluation of the structure-activity relationship (SAR) and the biological activities of the compounds were determined with a luminescent cell viability assay. The identified leading compound, Stemazole, exhibited remarkable proliferation-promoting activity in human hippocampal stem/progenitor cells (HSCs) in a time-dependent and concentration-dependent manner. The proliferation-promoting activity of Stemazole was further confirmed against a panel of human stem/progenitor cells derived from each of the three blastoderm layers. In conclusion, Stemazole is a novel activator of stem cells proliferation.
- Sun, Ying,Wang, Wei,Sun, Yuanyuan,Han, Mei
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experimental part
p. 2930 - 2936
(2011/06/27)
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- NOVEL COMPOUNDS EFFECTIVE AS XANTHINE OXIDASE INHIBITORS, METHOD FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME
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The present invention relates to novel compounds which are effective as an inhibitor for xanthine oxidase, a process for preparing the same, and a pharmaceutical composition comprising a therapeutically effective amount of the same.
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Paragraph 1365-1368
(2010/09/03)
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- Nitrogen functionalities in palladium-catalyzed reactions on solid supports: A case study
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Three different Palladium-catalyzed reactions (Heck, Suzuki, Sonogashira) were carried out on three different types of linkers on solid supports. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Knepper, Kerstin,Vanderheiden, Sylvia,Braese, Stefan
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p. 1886 - 1898
(2007/10/03)
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- INDOLE DERIVATIVES AS 5-HT1 AGONISTS
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Compounds of the formula (I) where A represents a direct bond, C 1-C 4 alkyl, or C 1-C 4 alkenyl; n is 0, 1, or 2; W, X, Y, and Z are each independently oxygen, sulfur, nitrogen or carbon, provided that at least one of W, X, Y, or Z is nitrogen. These compounds are useful psychotherapeutics and are potent serotonin (5-HT 1) agonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain and chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission. The compounds can also be used as centrally acting antihypertensives and vasodilators.
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