- Ligand- and Counterion-Assisted Phenol O-Arylation with TMP-Iodonium(III) Acetates
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High reactivity of trimethoxyphenyl (TMP)-iodonium(III) acetate for phenol O-arylation was achieved. It was first determined that the TMP ligand and acetate anion cooperatively enhance the electrophilic reactivity toward phenol oxygen atoms. The proposed method provides access to various diaryl ethers in significantly higher yields than the previously reported techniques. Various functional groups, including aliphatic alcohol, boronic ester, and sterically hindered groups, were tolerated during O-arylation, verifying the applicability of this ligand- and counterion-assisted strategy.
- Kikushima, Kotaro,Miyamoto, Naoki,Watanabe, Kazuma,Koseki, Daichi,Kita, Yasuyuki,Dohi, Toshifumi
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p. 1924 - 1928
(2022/03/27)
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- Nickel-Catalyzed C-O Cross-Coupling Reaction at Low Catalytic Loading with Weak Base Participation
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Herein, we report a nickel-catalyzed crossing-coupling reaction for the synthesis of diaryl ethers. The desired products are achieved by coupling heterocyclic alcohols with aryl bromides bearing strong electron withdrawing nitro group under the catalyst system of NiCl2(PPh3)2 and weak base KHCO3. This mild reaction exhibits a broad functional group tolerance. Compound 4 as an important intermediate is suitable for further structural modification of MALT1 inhibitor MI-2.
- Wu, Fan,Zhu, Kejie,Wu, Guolin,Gao, Yu,Chen, Haijun
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supporting information
p. 519 - 522
(2020/01/30)
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- Structural optimization and structure–activity relationship of 4-thiazolidinone derivatives as novel inhibitors of human dihydroorotate dehydrogenase
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Human dihydroorotate dehydrogenase (hDHODH), one of the attractive targets for the development of immunosuppressive drugs, is also a potential target of anticancer drugs and anti-leukemic drugs. The development of promising hDHODH inhibitors is in high demand. Based on the unique binding mode of our previous reported 4-thiazolidinone derivatives, via molecular docking method, three new series 4-thiazolidinone derivatives were designed and synthesized as hDHODH inhibitors. The preliminary structure–activity relationship was investigated. Compound 9 of biphenyl series and compound 37 of amide series displayed IC50 values of 1.32 μM and 1.45 μM, respectively. This research will provide valuable reference for the research of new structures of hDHODH inhibitors.
- Zeng, Fanxun,Quan, Lina,Yang, Guantian,Qi, Tiantian,Zhang, Letian,Li, Shiliang,Li, Honglin,Zhu, Lili,Xu, Xiaoyong
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- AGRICULTURAL CHEMICALS
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The present invention relates to picolinic acid derivatives that are useful in treating fungal diseases ofplants.
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Page/Page column 56; 94
(2019/08/08)
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- Discovery of 1,2,4-triazole-1,3-disulfonamides as dual inhibitors of mitochondrial complex II and complex III
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Respiratory chain succinate-ubiquinone oxidoreductase (SQR or complex II) and ubihydroquinone-cytochrome (cyt) c oxidoreductase (cyt bc1 or complex III) have been demonstrated as the promising targets of numerous antibiotics and fungicides. As a continuation of our research work on the development of new fungicides, a series of 1,2,4-triazole-1,3-disulfonamide derivatives with dual functions targeting both SQR and cyt bc1 were designed and synthesized by coupling diverse diphenyl ether moieties with triazolesulfonamide units. These newly synthesized compounds were characterized by elemental analyses, 1H NMR and ESI-MS spectrometry. The in vitro assay indicated that most of the synthesized compounds displayed good inhibition against porcine succinate-cytochrome reductase (SCR) with IC50 values ranging from 3.2 to 81.8 μM, revealing much higher activity than that of the commercial control amisulbrom whose IC50 value is 93.0 μM. Further evaluation against the respective SQR and cyt bc1 indicated that most compounds exhibited SQR-inhibiting activity as well as cyt bc1-inhibiting activity, but the inhibition potency against SQR is much higher than that against cyt bc1, showing that the SCR inhibition might be contributed greatly by the SQR inhibition. The further antibacterial evaluation against Xanthomonas oryzae pv. oryzae revealed that four compounds showed excellent potency at the concentration of 20 μg mL-1. In particular, compounds 6h and 6j exhibited much better antibacterial activity than the commercial control bismerthiazol in terms of their EC50. Impressively, 6j has an EC90 of 33.62 μg mL-1, more than 10-fold higher than that of bismerthiazol.
- Cheng, Hua,Shen, Yan-Qing,Pan, Xia-Yan,Hou, Yi-Ping,Wu, Qiong-You,Yang, Guang-Fu
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p. 7281 - 7292
(2015/09/02)
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- Synthesis of diaryl ethers, diaryl sulfides, heteroaryl ethers and heteroaryl sulfides under microwave dielectric heating
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This paper describes the synthesis of diaryl ethers and sulfides by utilizing microwave heating methodology. The methodology is shown to be rapid and efficient for the coupling of phenols or thiophenol with electron-deficient aryl halides through a SNAr reaction. The scope of the protocol can be expanded to six-membered heterocycles bearing a hydroxyl group as well as to the reaction of 2-pyrimidinethiol with mildly activated aryl halides, providing heteroaryl ethers and sulfides, respectively. The advantages of the present method include the wide substrate scope, the obviation of metal catalysts, ease of product isolation, and high purity of products. Georg Thieme Verlag Stuttgart.
- Li, Feng,Meng, Qingqing,Chen, Huansheng,Li, Zhiming,Wang, Quanrui,Tao, Fenggang
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p. 1305 - 1313
(2007/10/03)
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- Derivatives of quinoline as inhibitors for MEK
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1. A compound of formula (I) or a pharmaceutically acceptable salt thereof. wherein: n is 0-1; X and Y are independently selected from -NH-, -O-, -S-, or -NR8- where R8 is alkyl of 1-6 carbon atoms and X may additionally comprise a CH2 group; R7 is a group (CH2)mR9 where m is 0,or an integer of from 1-3 and R9 is a substituted aryl group, an optionally substituted cycloalkyl ring of up to 10 carbon atoms, or an optionally substituted heterocyclic ring or an N-oxide of any nitrogen containing ring; R6 is a divalent cycloalkyl of 3 to 7 carbon atoms, which may be optionally further substituted with one or more alkyl of 1 to 6 carbon atom groups; or is a divalent pyridinyl, pyimidinyl, or phenyl ring; wherein the pyridinyl, pyrimidinyl, or phenyl ring may be optionally further substituted with one or more specified groups; R1, R2, R3 and R4 are each independently selected from hydrogen or various specified organic groups. Compounds are useful as pharmaceuticals for the inhibition of MEK activity.
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Page/Page column 49
(2010/02/14)
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- Pyrrolopyridazine compounds and methods of use thereof for the treatment of proliferative disorders
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Disclosed are pyrrolopyridazine compounds, methods of preparing such compounds, and their use for the treatment of proliferative, inflammatory, and other disorders.
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- 4-Substituted anilides as selective melatonin MT2 receptor agonists
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A series of 4-substituted anilides with human melatonergic affinity is reported. Butyramides 26, 39, 42, 52, 57, and 58 all demonstrated subnanomolar MT2 binding affinity and MT2 selectivity of at least 70-fold over the MT1 receptor. Compound 26 demonstrated full agonism at the MT2 receptor.
- Epperson, James R.,Deskus, Jeffrey A.,Gentile, Anthony J.,Iben, Lawrence G.,Ryan, Elaine,Sarbin, Nathan S.
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p. 1023 - 1026
(2007/10/03)
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- Microwave assisted aromatic nucleophilic substitution reaction under solventless condition
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We report here microwave assisted aromatic nucleophilic substitution reaction of 1-chloro-4-nitrobenzene with different phenoxides.
- Rebeiro, Geeta L.,Khadilkar, Bhushan M.
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p. 1405 - 1410
(2007/10/03)
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- PHENOXENIUM IONS. IDENTICAL INTERMEDIATES IN THE ACID-CATALYZED SOLVOLYSIS OF N-TOSYL-O-ARYLHYDROXYLAMINES AND IN THE THERMOLYSIS OF N-ARYLOXYPYRIDINIUM SALTS
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The acid-catalyzed solvolysis of N-tosyl-O-arylhydroxylamines in aromatic solvents and the thermolysis of N-aryloxypyridinium salts involve common intermediates, phenoxenium ions, for the formation of hydroxybiphenyl derivatives.Diphenylethers are formed when the heterolysis of the N-O bonds is slow and the aromatic solvent has high nucleophilicity.
- Iijima, Hiroyuki,Endo, Yasuyuki,Shudo, Koichi,Okamoto, Toshihiko
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p. 4981 - 4986
(2007/10/02)
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- Aryloxenium Ions. Generation from N-(Aryloxy)pyridinium Tetrafluoroborates and Reaction with Anisole and Benzonitrile
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N-(Aryloxy)pyridinium tetrafluoroborates (4) decompose thermally at 180-200 deg C in anisole and benzonitrile to form products of intermolecular C-O-C and C-C bond formation.With anisole, diphenyl ethers (5) and hydroxybiphenyls (6) are formed; with benzonitrile, the main product is benzoxazole (14).A homolytic process was ruled out by showing that none of these products were formed when perbenzoyl p-nitrophenyl carbonate (18) was decomposed in these solvents.The main products in this case were those of homolytic phenylation (and benzoyloxylation with anisole).A concerted SN2-type heterolytic process was ruled out by showing that the nature of the substituent in the pyridine ring had no effect on the isomer ratios of 5 and 6 in the thermolysis of 4 (X = p-NO2) in anisole.The results are explained in terms of a unimolecular heterolysis of 4 to give the pyridine and aryloxenium ion 2 which now attacks solvent molecules.When an electron-withdrawing substituent is present in 2, more C-O-C than C-C products are formed in anisole.When it is absent only products of C-C bond formation are found.PhO+ is apparently electrophilic enough to attack anisole and give the four possible hydroxymethoxybiphenyls (10-13).
- Abramovitch, Rudolph A.,Alvernhe, Gerard,Bartnik, Romuald,Dassanayake, Nissanke L.,Inbasekaran, Mutiah N.,Kato, Shiego
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p. 4558 - 4565
(2007/10/02)
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