30609-20-2Relevant academic research and scientific papers
Design and optimisation of a small-molecule TLR2/4 antagonist for anti-tumour therapy
Chen, Hekai,Kong, Jun,Li, Tian,Xu, Qun,Yin, Hang,Zhang, Liwei
supporting information, p. 1771 - 1779 (2021/11/19)
In anti-tumour therapy, the toll-like receptor 2/4 (TLR2/4) signalling pathway has been a double-edged sword. TLR2/4 agonists are commonly considered adjuvants for immune stimulation, whereas TLR2/4 antagonists demonstrate more feasibility for anti-tumour therapy under specific chronic inflammatory situations. In individuals with cancer retaliatory proliferation and metastasis after surgery, blocking the TLR2/4 signalling pathway may produce favourable prognosis for patients. Therefore, here, we developed a small-molecule co-inhibitor that targets the TLR2/4 signalling pathway. After high-throughput screening of a compound library containing 14 400 small molecules, followed by hit-to-lead structural optimisation, we finally obtained the compound TX-33, which has effective inhibitory properties against the TLR2/4 signalling pathways. This compound was found to significantly inhibit multiple pro-inflammatory cytokines released by RAW264.7 cells. This was followed by TX-33 demonstrating promising efficacy in subsequent anti-tumour experiments. The current results provide a novel understanding of the role of TLR2/4 in cancer and a novel strategy for anti-tumour therapy.
ALKOXYBENZALDEHYDE DERIVATIVES AND PRECURSORS THEREOF
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Page/Page column 12-13, (2020/05/29)
The present invention refers to alkoxybenzaldehyde derivatives and precursors thereof. The invention further refers to perfume compositions and fragranced article comprising them.
PROCESS FOR THE PRODUCTION OF SUBSTITUTED 2-[2-(PHENYL) ETHYLAMINO]ALKANEAMIDE DERIVATIVES
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Page/Page column 9-10; 8, (2020/10/28)
The present invention relates to a new process for the production of substituted 2-[2-(phenyl) ethylaminojalkaneamide derivatives of the following formula (I), in particular 2-[2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylacetamide in high yields with very
PROCESS FOR THE PRODUCTION OF SUBSTITUTED 2-[2-(PHENYL) ETHYLAMINO]ALKANEAMIDE DERIVATIVES
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Page/Page column 15; 16, (2020/10/28)
The present invention refers to a process for preparing a compound of formula (I) or a pharmaceutically acceptable salt thereof: wherein R is (C3-C10)alkyl, or ω-trifluoro(C3-C10)alkyl; R1 and R2 are, independently, hydrogen, hydroxy, (C1-C8) alkoxy, (C1-C8) alkylthio, halo, trifluoromethyl or 2,2,2-trifluoroethyl; or one of R1 and R2 is in ortho position to the R-O- group and, taken together with the same R-O-, represents a Formula (A) group where Ro is (C2-C9)alkyl; R3 and R4 are, independently, hydrogen, (C1-C4)alkyl; or R4 is hydrogen and R5 is a group selected from -CH2-OH, -CH2-O-(C1-C6)alkyl, -CH(CH3)-OH, -(CH2)2-S-CH3, benzyl and 4-hydroxybenzyl; or R4 and R5, taken together with the adjacent carbon atom, form a (C3-C6)cycloalkyl residue; R5 and R6 are independently hydrogen or (C1-C6)alkyl; or taken together with the adjacent nitrogen atom form a 5-6 membered monocyclic saturated heterocycle, optionally containing one additional heteroatom chosen among -O-, -S- and -NR7- where R7 is hydrogen or (C1-C6) alkyl; and wherein optionally one or more hydrogen atom in the groups R, R1, R2, R3, R4, R5 and R6, preferably in the R group, can be substituted by a deuterium atom.
Synthesis and Structure–Activity Relationships of Novel Benzylamine-Type Antifungals as Butenafine-Related Antimycotics
Krauss, Jürgen,Stadler, Martina,Bracher, Franz
, (2017/05/05)
Benzylamine-type antimycotics like naftifine, butenafine, or terbinafine are a well-known class of antimycotics since the 1980s. The following paper describes the synthesis and biological evaluation of a series of novel benzylamine-type antimycotics characterized by an isooctyl side chain and various substituents at the benzylamine moiety. The compounds were prepared from benzaldehyde derivatives and 2-amino-6-methylheptane by reductive amination with sodium triacetoxyborohydride and subsequent precipitation with hydrogen chloride. The antimycotic activity of the resulting compounds was evaluated in an agar diffusion assay against the yeasts C. glabrata and Yarrowia lipolytica, the mold Aspergillus niger and the dermatophyte H. burtonii. The compounds were also tested in a microdilution assay against the yeast Candida glabrata and the dermatophyte H. burtonii to determine the minimal inhibitory concentrations (MIC). Compounds with an aromatic ether side chain or a short alkyl ether side chain showed significant antimycotic activity against C. glabrata, comparable to terbinafine or clotrimazole.
Organic soluble indigoids derived from 3-hydroxybenzaldehyde for N-type organic field-effect transistor (OFET) applications
Ngai, Jenner H.L.,Leung, Louis M.,So,Lee, Harrison K.H.
, p. 258 - 266 (2016/03/15)
Two new series of organic soluble indigoids 7-7′-dialkoxyindigoids (2a, 2b) and 4,4′-dibromo-7,7′-dialkoxyindigoids (3a, 3b) (alkoxy = n-butoxy and n-octyloxy) were synthesized starting from the inexpensive 3-hydroxybenzaldehyde. The indigoids were solubl
NOVEL SUGAR-DERIVED GELATOR
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Paragraph 0133; 0134; 0143, (2015/02/18)
There is provided a novel gelator containing a sugar derivative. A gelator including a compound of Formula (1) or Formula (2): wherein each of R1 and R3 is independently a linear or branched alkyl group having a carbon atom number of 1 to 20, a cyclic C3-20 alkyl group, or a linear or branched alkenyl group having a carbon atom number of 2 to 20, n is 0 or an integer of 1 to 4, R2 is a hydrogen atom, a linear or branched alkyl group having a carbon atom number of 1 to 10, or an aryl group optionally having a substituent, and R4 and R5 are each a hydroxy group.
Mild One-Step Synthesis of 4,6-Benzylideneglycopyranosides from Aromatic Aldehydes and Gelation Abilities of the Glucose Derivatives
Ono, Fumiyasu,Hirata, Osamu,Ichimaru, Keiko,Saruhashi, Koichiro,Watanabe, Hisayuki,Shinkai, Seiji
supporting information, p. 6439 - 6447 (2015/10/19)
We report herein an efficient one-step synthesis of 4,6-benzylidene glycoside derivatives from aromatic aldehydes bearing electron-donating or -withdrawing groups as well as polymerisable monomer groups. Glucose, mannose and galactose derivatives could also be used successfully. Several of the glucose derivatives thus obtained acted as gelators for various solvents, including water. 4-(n-Butoxybenzylidene)glucose derivative 3a produced both a clear squalane gel and a hydrogel at 0.1 wt.-%. Furthermore, 3-(n-butoxybenzylidene)glucose derivative 3i produced a clear organogel and an opaque hydrogel. The critical gelation concentration (CGC) of 3i in squalane was determined to be 0.02 wt.-%, which is one of the lowest CGC values reported so far. The organogels, hydrogels and aqueous solution gels produced from 3a and 3d exhibited thixotropy. The strength and thixotropy of the organo- and hydrogel produced from 3a were estimated by a rheometer. The gel morphologies were observed by field-emission and wet-scanning electron microscopy, and the self-assembly modes were analysed by XRD. We have concluded that super-gelators can be created by this method. An efficient one-step synthesis of 4,6-benzylidene glycosides from aromatic aldehydes under mild conditions has been achieved. Some of the glucose derivatives synthesised by this method produced clear organo- and hydrogels with thixotropic properties. The critical gelation concentrations of the gels were below 0.1 wt.-%.
Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors
Nishikawa, Keisuke,Fukuda, Hiroshi,Abe, Masato,Nakanishi, Kazunari,Taniguchi, Tomoya,Nomura, Takashi,Yamaguchi, Chihiro,Hiradate, Syuntaro,Fujii, Yoshiharu,Okuda, Katsuhiro,Shindo, Mitsuru
, p. 132 - 147 (2014/01/06)
1-O-cis-Cinnamoyl-β-d-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA.
3,4-DIHYDROPYRIMIDINE TRPA1 ANTAGONISTS
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Page/Page column 15-16, (2009/12/28)
The present invention is related to novel 3,4-dihydropyrimidine compounds of formula (I) having TRPA1 receptor antagonistic properties, pharmaceutical compositions comprising these compounds, chemical processes for preparing these compounds and their use
