- Synthesis of fused tetrazolone derivatives
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New fused tetrazolone derivatives were synthesized using homophthalic and maleic anhydrides. Treatment of anhydrides with trimethylsilyl azide opened the lactone rings and formed the corresponding intermediates, which bore 1,3-dipole and dipolarophile functionalities in ortho positions. The intermediates partially underwent internal 1,3-dipolar cycloaddition to produce fused tetrazolone derivatives. When the carbonyl groups in anhydride were not conjugated with any double bond, then a triazine-fused tetrazolone derivative was formed. TUeBITAK.
- Oezcan, Sevil,Ekmekci, Zeynep,Muejde, Berk,Balci, Metin
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Read Online
- Synthesis of 3-Ferrocenyl Isocoumarins
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The derivatives of 3-ferrocenyl isocoumarin were synthesized by the condensation of substituted homothphalic anhydride with ferrocene using phosphoric acid or anhydrous aluminium chloride as cyclising agent. Substituted homophthalic acid did not condense with ferrocene so homophthalic acids were converted into their anhydride and then allowed to react with ferrocene in the presence of polyphosphoric acid or in the presence of anhydrous aluminium chloride using dichloromethane as the solvent to give 3-ferrocenyl isocoumarins. 7-Methoxy, 6-methyl, 5,7-dihydroxy, 6,7-dimethoxy and 5,7-dimethoxy derivatives of 3-ferrocenyl isocoumarin were synthesized. All the compounds were characterised by melting point determination, elemental and spectral analysis.
- Sinha, Neeta
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p. 976 - 979
(2020/11/25)
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- Highly Enantio- and Diastereoselective Catalytic Asymmetric Tamura Cycloaddition Reactions
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The first broad-scope catalytic asymmetric Tamura cycloaddition reactions are reported. Under the influence of anion-binding bifunctional catalysis a wide range of α,β-unsaturated N-trityl imines undergo reactions with enolisable anhydrides to form highly synthetically useful α-tetralone structures with excellent enantio- and -diastereocontrol. In stark contrast to the previous literature benchmarks, doubly activated or highly electron deficient alkenes are not required. A facile two-step, high yielding sequence can convert the cycloadducts to α-haloketones (challenging to generate catalytically by other means) with the net formation of two new C?C bonds and three new contiguous stereocentres with exquisite stereocontrol. A DFT study has provided insight into the catalyst mode of action and the origins of the observed enantiocontrol.
- Collar, Aarón Gutiérrez,Trujillo, Cristina,Connon, Stephen J.
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supporting information
p. 7270 - 7274
(2019/05/15)
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- Design, synthesis and biological evaluation of 3-substituted indenoisoquinoline derivatives as topoisomerase I inhibitors
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A new series of indenoisoquinoline derivatives was designed and synthesized. The in vitro anti-proliferative activity of these novel compounds was evaluated in HepG2, A549 and HCT-116 cell lines. Compounds 9a, 9b, 10a, 10c, 10e, 18a and 18b manifested potent inhibitory activity against the three tested cancer cell lines. Nineteen compounds were also tested for Top I inhibition at 50 μM. Almost all the tested compounds showed potent Top I inhibition activity at this concentration. The most potent compounds 9a and 10a demonstrated more cytotoxicity than HCPT and TPT and was comparable to CPT in inhibitory activities on Top I in our biological assay.
- Zhao, Qian,Xu, Xi,Xie, Zhouling,Liu, Xiao,You, Qidong,Guo, Qinglong,Zhong, Yi,Li, Zhiyu
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p. 1068 - 1072
(2016/05/24)
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- Design, synthesis and evaluation of 6-aryl-indenoisoquinolone derivatives dual targeting ERα and VEGFR-2 as anti-breast cancer agents
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The estrogen receptors have played important roles in breast cancer development and progression. Selective estrogen receptor modulators, such as Tamoxifen, have showed great benefits in the treatment and prevention of breast cancer. But the disadvantages of induction of endometrial cancer and drug resistance have limited their use. Multiple ligand which act at multiple biomolecular targets may exert favorable advantages of improved efficacy with lower incidence of side effects. In this work, we described the synthesis and evaluation of a series of 6-aryl-indenoisoquinolone derivatives as dual ERα and VEGFR-2 inhibitors. These compounds presented good ERα binding affinity and ERα antagonistic activity, as well as potent VEGFR-2 inhibitory potency. They also possessed excellent anti-proliferative activities against MCF-7, MDA-MB-231, Ishikawa and HUVEC cell lines. Further investigation of selective compound 21c showed that it was able to inhibit the activation of VEGFR-2 and the signaling transduction of Raf-1/MAPK/ERK pathway in MCF-7 cells.
- Tang, Zhichao,Wu, Chengzhe,Wang, Tianlin,Lao, Kejing,Wang, Yejun,Liu, Linyi,Muyaba, Moses,Xu, Pei,He, Conghui,Luo, Guoshun,Qian, Zhouyang,Niu, Shaoxiong,Wang, Lijun,Wang, Ying,Xiao, Hong,You, Qidong,Xiang, Hua
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p. 328 - 339
(2016/06/01)
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- INDENOISOQUINOLINONE DERIVATIVES, MANUFACTURING METHOD AND MEDICAL USE THEREOF
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Indenoisoquinolinone derivatives (I), the manufacturing method and the medical use thereof, which belong to pharmaceutical chemistry and organic chemistry field, are disclosed. These compounds can be used for treating several medical symptoms related to postmenopausal syndrome, uterine fibers deterioration and aortic smooth muscle cells proliferation, especially ER-(+) depend breast cancer. Meanwhile, these compounds can also be used for treating glioma and lung cancer, and have inhibiting effect on tumor metastasis effect on tumor metastasis.
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Paragraph 0041; 0042
(2013/04/13)
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- ENANTIOSELECTIVE ORGANIC ANHYDRIDE REACTIONS
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Disclosed herein is enantioselective synthetic method comprising reacting an enolisable C4-C50 organic anhydride with a second compound selected from the group consisting of an aldehyde, a ketone, an aldimine, a ketimine or a Michael Acceptor in the presence of a bifunctional organocatalyst. The reaction may find particular utility in the enantioselective synthesis of medicinally relevant heterocycles, such as dihydroisocoumarins and dihydroisoquinolinones.
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(2013/09/26)
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- A catalytic asymmetric reaction involving enolizable anhydrides
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In the presence of a highly efficient novel bifunctional organocatalyst at low loadings under mild conditions, enolizable homophthalic anhydrides can be added to a range of aromatic and aliphatic aldehydes to give dihydroisocoumarins, with excellent yields and diastereo-and enantiocontrol (up to 99% ee).
- Cornaggia, Claudio,Manoni, Francesco,Torrente, Esther,Tallon, Sean,Connon, Stephen J.
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supporting information; scheme or table
p. 1850 - 1853
(2012/06/16)
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- Synthesis of indolin-2-one, isoindolin-1-one, and indole derivatives from homophthalic acid
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We hereby report the preparation of indolin-2-one and isoindolin-1-one and their derivatives starting from 2-(carboxymethyl)benzoic acid, which was first regiospecifically converted into the isomeric half esters. Transformation of the acid functionalities to the acyl azides followed by Curtius rearrangement gave the regioisomeric isocyanates. Reaction of the isocyanates with aniline produced urethane derivatives. Intramolecular cyclization provided the target compounds. Georg Thieme Verlag Stuttgart. New York.
- Kilikli, Alper A.,Dengiz, Cagatay,Oezcan, Sevil,Balci, Metin
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experimental part
p. 3697 - 3705
(2011/12/21)
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- A novel one-pot, three-component reaction for the synthesis of isocoumarin-condensed pyrazoles
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The one-pot, three-component reaction of substituted homophthalic anhydrides with hydrazine in DMF as solvent and reactant, at reflux temperature, afforded isochromeno[3,4-c]pyrazole-5(2H)-one derivatives in high yields. The mechanism and roles of the substrates were investigated and it was found that cyclic hydrazides were formed as intermediates.
- Ozcan, Sevil,Dengiz, Cagatay,Deli?meroglu, Murat K.,Sahin, Ertan,Balci, Metin
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supporting information; experimental part
p. 1495 - 1497
(2011/05/16)
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- ISOQUINOLINE DERIVATIVES AND THEIR USE AS INHIBITORS OF CYTOKINE MEDIATED DISEASES
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The invention concerns a compound of formula (I) or pharmaceutically-acceptable salts thereof wherein R1, R2, R3, R4, R5 and m are as defined in the specification, processes for their preparation, pha
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Page/Page column 52
(2008/06/13)
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- AMIDE DERIVATIVES
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The invention concerns a compound of the Formula I (A chemical formula should be inserted here - please see paper copy enclosed herewith) wherein m is 0-2 and each R1 is a group such as hydroxy, halogeno, trifluoromethyl heterocyclyl and heterocyclyloxy; R2 is halogeno, trifluoromethyl or (1-6C)alkyl; R3 is hydrogen, halogeno or (1-6C)alkyl; and R4 is (3-6C)cycloalkyl;or pharmaceutically-acceptable salts thereof; processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases or medical condions mediated by cytokines.
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Page/Page column 53-55
(2008/06/13)
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