- Understanding the cytotoxic effects of new isovanillin derivatives through phospholipid Langmuir monolayers
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Twenty-one isovanillin derivatives were prepared in order to evaluate their cytotoxic properties against the cancer cell lines B16F10-Nex2, HL-60, MCF-7, A2058 and HeLa. Among them, seven derivatives exhibited cytotoxic activity. We observed that for obtaining smaller IC50 values and for increasing the index of selectivity, two structural features are very important when compared with isovanillin (1); a hydroxymethyl group at C-1 and the replacement of the hydroxyl group at C-3 by different alkyl groups. As the lipophilicity of the compounds was changed, we decided to investigate the interaction of the cytotoxic isovallinin derivatives on cell membrane models through Langmuir monolayers by employing the lipids DPPC (1,2-diplamitoyl-sn-glycero-3-phosphocoline) and DPPS (1,2-diplamitoyl-sn-glycero-3-phosphoserine). The structural changes on the scaffold of the compounds modulated the interaction with the phospholipids at the air-water interface. These results were very important to understand the biophysical aspects related to the interaction of the cytotoxic compounds with the cancer cell membranes.
- de Carvalho, Ana C.,Girola, Natália,de Figueiredo, Carlos R.,Machado, André C.,de Medeiros, Lívia S.,Guadagnin, Rafael C.,Caseli, Luciano,Veiga, Thiago A.M.
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p. 205 - 213
(2018/11/01)
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- Concurrent synthesis of vanillin and isovanillin
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A method for concurrent synthesis of vanillin and isovanillin has been developed by a nonregioselective Vilsmeier-Haack reaction of O-alkyl guaiacols. O-Alkylation of guaiacol provided the corresponding O-alkyl guaiacol (1), which was then formylated with N-methylformanilide/phosphorus oxychloride to give a mixture of 4-alkoxy-3-methoxy-benzaldehyde (2) and 3-alkoxy-4- methoxybenzaldehyde (3). Finally, the obtained mixture underwent a selective dealkylation by anhydrous aluminium trichloride, while leaving methyl groups intact to simultaneously achieve the significant fine chemicals vanillin and isovanillin.
- Huang, Wei-Bin,Du, Cai-Yan,Jiang, Jian-An,Ji, Ya-Fei
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p. 2849 - 2856
(2013/07/26)
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- Discovery and structural modification of 1-phenyl-3-(1-phenylethyl)urea derivatives as inhibitors of complement
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A series of 1-phenyl-3-(1-phenylethyl)urea derivatives were identified as novel and potent complement inhibitors through structural modification of the original compound from high-throughput screening. Various analogues (7 and 13-15) were synthesized and identified as complement inhibitors, with the introduction of a five- or six-carbon chain (7c, 7d, 7k, 7l, and 7o) greatly improving their activity. Optimized compound 7l has an excellent inhibition activity with IC50 values as low as 13 nM. We demonstrated that the compound 7l inhibited C9 deposition through the classical, the lectin, and the alternative pathways but had no influence on C3 and C4 depositions.
- Zhang, Mei,Yang, Xiao-Ying,Tang, Wei,Groeneveld, Tom W. L.,He, Pei-Lan,Zhu, Feng-Hua,Li, Jia,Lu, Wei,Blom, Anna M.,Zuo, Jian-Ping,Nan, Fa-Jun
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supporting information; experimental part
p. 317 - 321
(2012/05/20)
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- PYRIMIDINE AND QUINAZOLINE DERIVATIVES
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This invention is concerned with compounds of the formula ( l ) wherein A, R1 to R5 and G are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.
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Page/Page column 78-79
(2008/06/13)
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- PYRIDINE, QUINOLINE AND PYRIMIDINE DERIVATIVES
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This invention is concerned with compounds of the formula wherein A, R1 to R5 are as defined in the specification and G is a pyridine, quinoline or pyrimidine group as defined in the specification, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.
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Page/Page column 29
(2008/06/13)
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- BENZOIMIDAZOLE, TETRAHYDRO-QUINOXALINE, BENZOTRIAZOLE, DIHYDRO-IMIDAZO[4,5-c] PYRIDINONE AND DIHYDRO-ISOINDOLONE DERIVATIVES
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This invention relates to compounds of the formula wherein A, R1 to R3 are as defined in the specification and G is benzoimidazole, quinoxaline, benzotriazole, dihydro-imidazo[4,5-c]pyridine and dihydro-isoindolone group as defined in the specification, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.
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Page/Page column 28
(2008/12/08)
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- 4,4-DISUBSTITUTED PIPERIDINE DERIVATIVES
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This invention relates to 4,4-disubstituted piperidine derivatives of the formula wherein A and R1 to R5 are as defined in the specification, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceuti
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Page/Page column 19
(2009/01/20)
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- PHENYL, PYRIDINE, QUINOLINE, ISOQUINOLINE, NAPHTHYRIDINE AND PYRAZINE DERIVATIVES
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This invention is concerned with compounds of the formulaand pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.
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Page/Page column 78-79
(2008/06/13)
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- 4,4-DISUBSTITUTED PIPERIDINE DERIVATIVES
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This invention relates to 4,4-disubstituted piperidine derivatives of the formula (I) wherein A and R1 to R5 are as defined in the specification, and pharmaceutically acceptable salts thereof. The invention further relates to pharmac
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Page/Page column 40
(2009/01/20)
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- Pyrimidine, quinazoline, pteridine and triazine derivatives
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This invention is concerned with compounds of the formula wherein A, R1 to R5 and G are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.
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Page/Page column 49
(2008/06/13)
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- Benzothiazole, thiazolopyridine, benzooxazole and oxazolopyridine derivatives
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This invention is concerned with compounds of the formula wherein A, B1, B2, R1, R2 and G are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.
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Page/Page column 30
(2010/11/23)
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- Compositions containing aromatic aldehydes and their use in treatments
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Disclosed are pharmaceutical and cosmetic compositions containing aromatic aldehyde compounds. Some of the disclosed compositions are useful as topical therapeutics for treating inflammatory dermatologic conditions. Some of the compositions are useful in transdermal and other systemic dose forms for treating other inflammatory conditions in mammals.
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- 6-phenyltetrahydro-1,3-oxazin-2-one derivative and pharmaceutical composition containing the same
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A 6-phenyltetrahydro-1,3-oxazin-2-one derivative having the formula (I): wherein, R1is an unsubstituted or substituted C1to C8alkyl group; an unsubstituted or substituted C3to C7cycloalkyl group;, etc
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- Use of 2-phenylmorpholin-5-one derivatives
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A 2-phenylmorpholin-5-one derivative having the formula (I): wherein R1 represents a C1 to C8 alkyl group, a C3 to C7 cycloalkyl group or an indanyl group, R2 represents a C1 to C4 alkyl group, R3 represents a hydrogen atom, a C1 to C5 alkyl group, etc., R4 represents a hydrogen atom, a C1 to C6 alkyl group, etc., R5, R6 represent a hydrogen atom, a C1 to C5 alkyl group, etc.,an optical isomer thereof or a pharmacologically acceptable salt thereof, or a hydrate or solvate thereof and a pharmaceutical composition containing the same.The above compound has a strong type IV phosphodiesterase (PDE) inhibitory activity and has bronchodilater and antiinflammatory effects.
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- 5-phenyl-3-pyridazinone derivatives and drug composition containing the same
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A 5-phenyl-3-pyridazinone derivative having the formula (I) wherein R1represents an unsubstituted or substituted C1to C8alkyl group, C3to C7cycloalkyl group, or indanyl group; R2represents
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- Selective Type IV Phosphodiesterase Inhibitors as Antiasthmatic Agents. The Syntheses and Biological Activities of 3-(Cyclopentyloxy)-4-methoxybenzamides and Analogues
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The syntheses and biological activities of a number of benzamide derivatives, designed from rolipram, which are selective inhibitors of cyclic AMP-specific phosphodiesterase (PDE IV), are described.The effects of changes to the alkoxy groups, amide linkag
- Ashton, Michael J.,Cook, David C.,Fenton, Garry,Karlsson, Jan-Anders,Palfreyman, Malcolm N.,et al.
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p. 1696 - 1703
(2007/10/02)
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