102-92-1Relevant articles and documents
Synthesis, and biological evaluation of new 1,3,4-thiadiazolium-2-phenylamine derivatives against Leishmania amazonensis promastigotes and amastigotes
Da Silva, Edson F.,Canto-Cavalheiro, Marilene M.,Braz, Viviane R.,Cysne-Finkelstein, Lea,Leon, Leonor L.,Echevarria, Aurea
, p. 979 - 984 (2002)
1,3,4-Thiadiazolium-2-aminide, which is a class of mesoionic compounds, were tested against promastigote and amastigote forms of Leishmania amazonensis. Parasites were assayed with or without the drugs in axenic media, using pentamidine isethionate as a reference drug. The very promising results showed us the most active compounds were the 4′- and 3′-methoxy derivatives against promastigote forms, while the highest activity against the amastigote forms was obtained with the 4′-fluor and 3′-bromo derivatives.
Role of phenoxy radicals in PCDD/F formation
Sidhu, Sukh,Edwards, Phil
, p. 531 - 541 (2002)
In this work, the role of phenoxy radicals in polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans (PCDD/F) formation was investigated by studying the slow oxidation of 2-chlorophenol (2-CP) and 2-chloroanisole (2-CA) at a gas-phase concentration of 4 ppm (~2.1 × 104 μg/m3) over a temperature range of 400-800°C. Residence times were maintained at 2.0 ± 0.10 s. PCDD/F reaction products were dibenzofuran, dibenzo-p-dioxin, 4-chlorodibenzofuran, 1-chlorodibenzo-p-dioxin, 4,6-dichlorodibenzofuran, and 1,6-dichlorodibenzo-p-dioxin (1,6-DCDD). Major products observed in these experiments were 2,6-dichlorophenol, 3-phenyl-2-propenal, 1-indanone, 1,3-isobenzofurandione, and 3-phenyl-2-propenoyl chloride. The 2-CP and 2-CA experiments, along with the variable concentration 2-CA experiments, showed that the concentration of radicals present in the oxidation system has a significant effect on the PCDD/F product distribution and ultimately the PCDD/PCDF ratio. Also, the observation of dichlorinated phenoxy phenol and dichlorinated dihydroxybiphenyl, the proposed intermediate species in the radical-radical mechanism, suggests that radical-radical mechanism dominates gas-phase PCDD/F formation. This information will be helpful in constructing a detailed kinetic mechanism of PCDD/F formation/destruction in combustor postcombustion zone.
A synthesis of cinnamoyloxyisoflavones
Aitmambetov,Tokhtybaeva,Tlegenov,Tsao
, p. 402 - 403 (2006)
Interaction of 7-hydroxyisoflavonones with cinnamoyl chloride results in cinnamoyloxyisoflavonones. Pleiades Publishing, Inc., 2006.
A Novel, Nonoxidative Method for the Conversion of Aldehydes to Esters
Wilson, Stephen R.,Tofigh, Soosan,Misra, Raj N.
, p. 1360 - 1361 (1982)
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Kharasch,Kane,Brown
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Novel 4-(4-substituted amidobenzyl)furan-2(5H)-one derivatives as topoisomerase I inhibitors
Peng, Cheng-Kang,Zeng, Ting,Xu, Xing-Jun,Chang, Yi-Qun,Hou, Wen,Lu, Kuo,Lin, Hui,Sun, Ping-Hua,Lin, Jing,Chen, Wei-Min
, p. 187 - 199 (2017)
In this study, two series of novel 4-(4-substituted amidobenzyl)furan-2(5H)-one derivatives containing an α,β-unsaturated lactone fragment were synthesized and screened for Topo I inhibition and antitumor activity. The topoisomerase I inhibitory activities and cytotoxicities against three human cancer cell lines (MCF-7,Hela,A549) were evaluated. The results revealed that series 2, compounds bearing an exocyclic double bond on the furanone ring, generally showed more potent activity than series 1, compounds lacking an exocyclic double bond. Several compounds of series 2 possess significant Topo I inhibitory activity and potent antiproliferative activity against cancer cell lines. Further mechanism studies of the most active compound of series 2 (B-15) indicated that synthetic compounds can not only stabilize the drug-enzyme-DNA covalent ternary complex as well as camptothecin, but also interfere with the binding between Topo I and DNA. The binding patterns of these compounds with Topo I and structure-activity relationships are discussed.
BTISA-catalyzed Friedel-Crafts bimolecular cyclization of cinnamic acid under superelectrophilic solvation conditions
Posternak, Anna G.,Garlyauskayte, Romute Yu.,Yagupolskii, Lev M.
, p. 274 - 277 (2010)
Friedel-Crafts bimolecular cyclizations of cinnamic acid and cinnamoyl chloride with aromatic compounds in strong and superstrong acids in present of 1 mol% BTISA were investigated. It was demonstrated that catalytic amounts of this new superacid have essential effect on such type of reactions. Its use makes possible the preparation of indanones with quantitative yields.
Synthesis and biological evaluation of 2,2-dimethylbenzopyran derivatives as potent neuroprotection agents
Du, Fangyu,Zhou, Qifan,Fu, Xiaoxiao,Shi, Yajie,Chen, Yuanguang,Fang, Wuhong,Yang, Jingyu,Chen, Guoliang
, p. 2498 - 2508 (2019)
The development of novel neuroprotection agents is of great significance for the treatment of ischemic stroke. In this study, a series of compounds comprising 2,2-dimethylbenzopyran groups and cinnamic acid groups have been synthesized. Preferential combination principles and bioisostere that improved the neuroprotective effect of the compounds were identified for this series via biological activity assay in vitro. Meanwhile, a functional reversal group of the acrylamide amide resulted in the most active compounds. Among them, BN-07 significantly improved the morphology of neurons and obviously increased cell survival rate of primary neurons induced by oxygen glucose deprivation (OGD), superior to clinically used anti-ischemic stroke drug edaravone (Eda). Overall, our findings may provide an alternative strategy for the design of novel anti-ischemic stroke agents with more potency than Eda.
Semisynthetic hybrids of boswellic acids: A novel class of potential anti-inflammatory and anti-arthritic agents
Chaturvedi, Devdutt,Dwivedi, Parmesh Kumar,Chaturvedi, Amit K.,Mishra, Nisha,Siddiqui,Mishra, Vorenda
, p. 2799 - 2812 (2015)
A series of hybrid molecules 7-13 of boswellic acid (BA)/11-keto-β-boswellic acid (KBA) 1/2 with well-known anti-inflammatory drugs (i.e. aspirin, naproxen, ibuprofen and cinnamic acid) have been synthesized and evaluated for their anti-inflammatory and a
Synthesis, cytotoxic activity, and DNA binding properties of antitumor cis-1,2-dihydroxy-1,2-dihydrobenzo[b]acronycine cinnamoyl esters
Do, Quyen,Tian, Wen,Yougnia, Rodrigue,Gaslonde, Thomas,Pfeiffer, Bruno,Pierre, Alain,Leonce, Stephane,Kraus-Berthier, Laurence,David-Cordonnier, Marie-Helene,Depauw, Sabine,Lansiaux, Amelie,Mazinghien, Romain,Koch, Michel,Tillequin, Francois,Michel, Sylvie,Dufat, Hanh
, p. 1918 - 1927 (2009)
Monocinnamoyl esters at position 2 of (±)-cis-1,2-dihydroxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one and their acetyl derivatives at position 1 were prepared as stabilized analogues of the anticancer alkylating
Syntheses and biological activities of pyranyl-substituted cinnamates
Zhu, Jun,Majikina, Motoji,Tawata, Shinkichi
, p. 161 - 163 (2001)
Twenty-two kinds of pyranyl-substituted cinnamates were synthesized by the reaction of 4-hydroxy-6-(2-phenylethyl)-2H-pyran-2-one or 4-hydroxy-6-methyl-2H-pyran-2-one (HMP) with a variety of substituted cinnamic acids, and their antifungal and plant growth inhibitory activities were investigated. Among the compounds prepared, 6-methyl-2-oxo-2H-pyran-4-yl 3-(4-isopropylphenyl)propenoate (H5) showed the strongest antifungal activity against Rhizoctonia solani and Sclerotium dellfinii, and 6-methyl-2-oxo-2H-pyran-4-yl 3-(2-methylphenyl)propenoate (H2) had the highest plant growth inhibitory activity toward Brassica rapa.
Effect of azo and ester linkages on rod shaped Schiff base liquid crystals and their photophysical investigations
Selvarasu, Chinnaiyan,Kannan, Palaninathan
, p. 234 - 240 (2016)
Two new series of rod shaped Schiff base containing liquid crystal compounds with azo and ester linkages have been synthesized and characterized respectively. The rod like molecules containing cinnamate linkages with four different alkyl spacers (n?=?6, 8
Volume of Association of Charge-Transfer Interaction of 1-Methyl-3-(carbomethoxy)pyridinium Iodide and Sodium 8-Chlorotheophyllinate in Aqueous Solution
Williams, R. Kenneth
, p. 93 - 95 (1984)
Values have been obtained for the association constant for the interaction of sodium 8-chlorotheophyllinate with 1-methyl-3-(carbomethoxy)pyridinium iodide in aqueous solution at pH 7.0, I = 0.20, at various temperatures and pressures.From these data the apparent volume change on association is estimated to be Δ = -6.5 (+/-0.5) cm3mol-1 at 25 deg C.Values for the compressibility increment were obtained within the range of ΔK = (1.6-2.0) x 1E-9 Pa-1.Values were also obtained for the association constant of sodium 8-chlorotheophyllinate with the methyl ester of trans-cinnamic acid in a methanol and water mixture at 1-atm pressure.The results are interpreted in terms of the volume change to be expected on association due to ion pairing, and the approach of aromatic rings in water.
Solvent-free regioselective synthesis of novel isoxazoline and pyrazoline N-substituted saccharin derivatives under microwave irradiation
Saber, Aziza,Driowya, Mohsine,Alaoui, Soukaina,Marzag, Hamid,Demange, Luc,álvarez, Eleuterio,Benhida, Rachid,Bougrin, Khalid
, p. 31 - 40 (2016)
Novel isoxazoline and pyrazoline derivatives of N-substituted saccharin were synthesized in good yields by 1,3-dipolar cycloaddition of N-crotonoyl- or N-cinnamoylsaccharin as dipolarophile to arylnitrile oxides or nitrile imines using p-HAP300 as catalyst under solvent-free microwave conditions. In this process, the yields were significantly improved compared to classical conditions without alteration of the selectivity. The regioselectivity as well as the nonthermal specific microwave effect are discussed.
Synthesis and some CNS activities of new benzofuranylacryloylpiperazines
Dauzonne,Gillardin,Lepage,Pointet,Risse,Lamotte,Demerseman
, p. 53 - 59 (1995)
A series of novel benzofuranylacryloylpiperazines, which are structurally related to both cinnamamide derivatives and befuraline, have been prepared as their hydrochlorides. Their anticonvulsant and antidepressant activities against seizures induced by el
Phosphorus oxychloride in organic synthesis. Part 2. Synthesis of cinnamic acid arylamides
Avanesyan,Simonyan
, p. 99 - 100 (2001)
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Synthesis, characterization, and antimicrobial activity of novel heterocyclic compounds containing a ferrocene unit via Michael addition reaction
Liu, Yuting,Zhang, Hanli,Yin, Dawei,Chen, Dan
, p. 3793 - 3801 (2015)
A series of novel heterocyclic compounds containing a ferrocene unit were synthesized by reacting ferrocenylchalcone with pyrazolyl amine or triazolyl amine via Michael addition reaction. A novel synthetic route of ferrocenylchalcones was developed in whi
Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives
Li, Peng-Xiao,Liu, Guo-Yun,Liu, Ren-Min,Liu, Yue,Mu, Wen-Wen,Sun, Ya-Lei,Yang, Jie
, (2022/01/13)
This work deals with the design and synthesis of 18 barbituric acid derivatives bearing 1,3-dimethylbarbituric acid and cinnamic acid scaffolds to find potent anticancer agents. The target molecules were obtained through Knoevenagel condensation and acylation reaction. The cytotoxicity was assessed by the MTT assay. Flowcytometry was performed to determine the cell cycle arrest, apoptosis, ROS levels and the loss of MMP. The ratios of GSH/GSSG and the MDA levels were determined by using UV spectrophotometry. The results revealed that introducing substitutions (CF3, OCF3, F) on the meta- of the benzyl ring of barbituric acid derivatives led to a considerable increase in the antiproliferative activities compared with that of corresponding ortho- and para-substituted barbituric acid derivatives. Mechanism investigation implied that the 1c could increase the ROS and MDA level, decrease the ratio of GSH/GSSG and MMP, and lead to cell cycle arrest. Further research is needed for structural optimization to enhance hydrophilicity, thereby improve the biological activity of these compounds.
PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation
Wu, Xiaofang,Zhou, Lei,Li, Fangshao,Xiao, Jing
, p. 491 - 497 (2021/01/20)
A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.
Meta-substituted piperlongumine derivatives attenuate inflammation in both RAW264.7 macrophages and a mouse model of colitis
Gong, Zhaotang,Liu, Guoyun,Mu, Wenwen,Wang, Ziqing,Yang, Jie
, (2021/11/16)
Piperlongumine (PL) has been showed to have multiple pharmacological activities. In this study, we reported the synthesis of three series of PL derivatives, and evaluation of their anti-inflammatory effects in both lipopolysaccharide (LPS)-induced Raw264.7 macrophages and a dextran sulfate sodium (DSS)-induced mouse model of colitis. Our results presented that two meta-substituent containing derivatives 1–3 and 1–6, in which γ-butyrolactam replaced α,β-unsaturated δ-valerolactam ring of PL, displayed low cytotoxicity and effective anti-inflammatory activity. Molecular docking also showed that the meta-substituted derivative, compared with the corresponding ortho- or para-substituted derivative, had significant interactions with the amino acid residues of CD14, which was the core receptors recognizing LPS. In vitro and in vivo studies, 1–3 and 1–6 could inhibit the expression of pro-inflammatory cytokines, and the excessive production of reactive nitrogen species and reactive oxygen species. Oral administration of 100 mg/kg/day of 1–3 or 1–6 alleviated the severity of clinical symptoms of colitis in mice, and significantly reduced the colonic tissue damage to protect the colonic tissue from the DSS-induced colitis. These results suggested that meta-substituted derivatives 1–3 and 1–6 were potential anti-inflammatory agents, which may lead to future pharmaceutical development.