- Synthesis and SAR study of simple aryl oximes and nitrofuranyl derivatives with potent activity against Mycobacterium tuberculosis
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Background: Oximes and nitrofuranyl derivatives are particularly important compounds in medicinal chemistry. Thus, many researchers have been reported to possess antibacterial, antiparasitic, insecticidal and fungicidal activities. Methods: In this work, we report the synthesis and the biological activity against Mycobacterium tuberculosis H37RV of a series of fifty aryl oximes, ArCH=N-OH, I, and eight nitrofuranyl compounds, 2-nitrofuranyl-X, II. Results: Among the oximes, I: Ar = 2-OH-4-OH, 42, and I: Ar = 5-nitrofuranyl, 46, possessed the best activity at 3.74 and 32.0 μM, respectively. Also, 46, the nitrofuran compounds, II; X = MeO, 55, and II: X = NHCH2Ph, 58, (14.6 and 12.6 μM, respectively), exhibited excellent biological activities and were non-cytotoxic. Conclusion: The compound 55 showed a selectivity index of 9.85. Further antibacterial tests were performed with compound 55 which was inactive against Enterococcus faecalis, Klebisiella pneumonae, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhymurium and Shigel-la flexneri. This study adds important information to the rational design of new lead anti-TB drugs. Structure-activity Relationship (SAR) is reported.
- Calixto, Stephane Lima,Carvalho, Guilherme da Silva Louren?o,Coimbra, Elaine Soares,Granato, Juliana da Trindade,Louren?o, Maria Cristina da Silva,Wardell, James,da Costa, Cristiane Fran?a,de Souza, Marcus Vinicius Nora
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- Bioinspired Design Provides High-Strength Benzoxazine Structural Adhesives
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A synthetic strategy to incorporate catechol functional groups into benzoxazine thermoset monomers was developed, leading to a family of bioinspired small-molecule resins and main-chain polybenzoxazines derived from biologically available phenols. Lap-she
- Higginson, Cody J.,Malollari, Katerina G.,Xu, Yunqi,Kelleghan, Andrew V.,Ricapito, Nicole G.,Messersmith, Phillip B.
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supporting information
p. 12271 - 12279
(2019/08/01)
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- Synthesis of nitrogenated lignin-derived compounds and reactivity with laccases. Study of their application in mild chemoenzymatic oxidative processes
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The chemical synthesis of a series of lignin-derived nitrogenated compounds was performed in high yields (73-99%) through simple conventional chemical transformations starting from natural monomers such as vanillin, syringaldehyde or 3,4-dihydroxybenzaldehyde. The study of the vanillin-derived compounds as substrates for commercially available laccases from Trametes versicolor and Myceliophthora thermophila in oxidative transformations, generally led to the isolation of several dimeric species in high to excellent conversions (>70%), while for hydrazone derivatives a more rapidly oxidative coupling was evidenced by the formation of oligomers and/or polymers. Remarkably, vanillin was obtained due to the hydrolysis of some of the nitrogenated functional groups, such as the hydrazone or the hydrazono tetrazole. The three families of lignin-derived compounds can provide a great source of new laccase-mediator systems (LMS), the possibility of employing them for lignin modification being particularly attractive. Preliminary experiments showed promising levels of activity towards the oxidation of a monomer (veratryl alcohol, up to 70% conversion) and a dimer (adlerol, up to 22% conversion) lignin models, higher than those achieved with the natural vanillin and syringaldehyde (up to 7% conversion with veratryl alcohol and almost negligible conversion with adlerol), these processes being also highly influenced by the pH of the reaction medium.
- Albarrán-Velo, Jesús,López-Iglesias, María,Gotor, Vicente,Gotor-Fernández, Vicente,Lavandera, Iván
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p. 50459 - 50471
(2017/11/10)
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- Constructing novel dihydrofuran and dihydroisoxazole analogues of isocombretastatin-4 as tubulin polymerization inhibitors through [3+2] reactions
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[3+2] reactions play a key role in constructing various pharmaceutical moleculars. In this study, using Mn(OAc)3 mediated and 1,3-dipolar [3+2] cyclization reactions, 38 novel dihydrofuran and dihydroisoxazole analogues of isoCA-4 were synthesized as inhibitors of tubulin polymerization. Among them, compound 6g was found to be the most potent cytotoxic agents against PC-3 cells with IC50 value of 0.47 μM, and compound 5p exhibted highest activity on HeLa cells with IC50 vaule of 2.32 μM. Tubulin polymerization assay revealed that 6g was a dose-dependent and effective inhibitor of tubulin assembly. Immunohistochemistry studies and cell cycle distribution analysis indicated that 6g severely disrupted microtubule network and significantly arrested most cells in the G2/M phase of the cell cycle in PC-3 cells. In addition, molecular docking studies showed that two chiral isomers of 6g can bind efficiently and similarly at colchicine binding site of tubulin.
- Song, Ming-Yu,Cao, Chen-Yu,He, Qiu-Rui,Dong, Qing-Miao,Li, Ding,Tang, Jiang-Jiang,Gao, Jin-Ming
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p. 5290 - 5302
(2017/10/06)
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- NITRONE COMPOUNDS AND THEIR USE IN PERSONAL CARE
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Provided are compounds and compositions thereof that are useful as antioxidants in personal care formulations. The compounds are of the Formula I: wherein R1, R2, R3, R4, R5, R6, R7/s
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Page/Page column 10; 11
(2015/11/02)
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- APPLICATIONS OF N6-SUBSTITUTED ADENOSINE DERIVATIVE AND N6-SUBSTITUTED ADENINE DERIVATIVE TO CALMING, HYPNOSES, CONVULSION RESISTANCE, EPILEPTIC RESISTANCE, PARKINSON DISEASE RESISTANCE, AND DEMENTIA PREVENTION AND TREATMENT
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PROBLEM TO BE SOLVED: To prepare analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. SOLUTION: The present invention relates to an N6-substituted adenosine derivative and an N6-substituted adenine derivative selected from the group consisting of specific compounds. The present invention also relates to a pharmaceutical composition at least comprising a therapeutically effective amount of the compounds and a pharmaceutically acceptable carrier. The invention further relates to the compounds used in preparation of analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. COPYRIGHT: (C)2016,JPO&INPIT
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Paragraph 0114
(2018/10/27)
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- N6-SUBSTITUTED ADENOSINE DERIVATIVES AND N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
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Paragraph 0157
(2013/03/26)
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- N6-SUBSTITUTED ADENOSINE DERIVATIVES, N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
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Page/Page column 49
(2012/11/06)
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- Biologically active hydroxymoyl chlorides as antifungal agents
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Several oximes and oxime ethers have been developed as antimicrobial agents. A series of chlorooximes (hydroximoyl chlorides) have been synthesized and tested for antifungal activity under in-vitro conditions against Candida albicans, Candida parapsilosis, Candida glabrata, Candida krusei, Aspergillus fumigatus, Aspergilhis flaviis and Aspergillus niger. The derived antifungal activity has been compared with the corresponding oximes. The results show that most of the chlorooximes exhibit potent antifungal activity with anti-isomers showing better activity. It is observed that most of the chlorooximes show interesting antifungal activity (MICs ≤ 32 μg/mL) compared to oximes. Compound 3q (2,3-dimethoxy phenyl hydroxymoyl chloride) is the most active compound. This compound is active against all the Candida species (MIC 0.5 μg/mL) as well as filamentous fungi with MIC range of 2-4 μg/mL. This series of compounds are fungicidal in nature as evident from the MFC results.
- Ismail, Tabasum,Shafi, Syed,Singh, Parvinder Pal,Qazi, Naveed Ahmed,Sawant, Sanghapal D.,Ali, Intzar,Khan, Inshad Ali,Kumar,Qazi, Ghulam Nabi,Alam, M. Sarwar
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p. 740 - 747
(2008/12/20)
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- Catechol oximes and their use in cosmetic and dermatological preparations
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The invention relates to cosmetic and/or dermatological preparations which contain, in part, novel catechol oximes of formula (I). Said preparations can promote, in physiological systems, the natural defense mechanisms against free radicals and reactive oxygen compounds, or can be used as protective agents in cosmetic or pharmaceutical products whose oxidation-sensitive constituents should be protected from autooxidation.
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- Hydroxy- or methoxy-substituted benzaldoximes and benzaldehyde-O-alkyloximes as tyrosinase inhibitors
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Several benzaldoximes, benzaldehyde-O-ethyloximes, and acetophenone-oximes were synthesized and evaluated as tyrosinase inhibitors by an assay based on tyrosinase catalyzed L-DOPA oxidation. Whereas benzaldoxime itself is only a weak inhibitor, its deriva
- Ley, Jakob P,Bertram, Heinz-Jürgen
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p. 1879 - 1885
(2007/10/03)
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