- Phloroglucinol derivatives as anti-tumor agents: synthesis, biological activity evaluation and molecular docking studies
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Phloroglucinol compounds isolated from Dryopteris fragrans (L.) Schott showed a variety of biological activities, such as anticancer and anti-inflammatory. In this study, we have made a number of modifications around the scaffold of phloroglucinol and synthesized phloroglucinol derivatives A1–A9, B1–B9, and C1–C3. We synthesized these compounds and investigated their effect on four human cancer cell lines (A-549, MCF-7, Hela, HepG2 cell lines) via MTT assay in vitro. The results revealed that all compounds exhibited certain antiproliferative activities on cancer cell lines and excellent inhibitory effects on MCF-7, in which compound C2 was the best with the IC50 value of 18.49 μM, exceeding that of 5-fluorouracil. Moreover, the cell apoptosis test showed that compound C2 induced apoptosis in a concentration-dependent manner. Furthermore, the results of molecular docking analysis explained the probable interaction between the active compounds and active sites of target protein 4I22 and 1OG5. [Figure not available: see fulltext.]
- Zhang, Fuli,Lai, Qingfu,Lai, Weihong,Li, Ming,Jin, Xiaobao,Ye, Lianbao
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p. 165 - 176
(2021/12/02)
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- Dihydropyrazole MurA enzyme inhibitor molecule as well as preparation method and application thereof
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The invention provides a dihydropyrazole MurA enzyme inhibitor molecule as well as a preparation method and application thereof. The structural formula is shown in the specification, R is a direct-connected alkyl group with the chemical formula of CnH2n+1, and n is equal to 1-7. The preparation method comprises the following steps of by taking acetophenone substances with different substituent groups and 4-(4-methyl piperazinyl) benzaldehyde as raw materials, carrying out aldol condensation reaction under an alkaline condition to obtain an intermediate, and synthesizing a target compound with a structural formula by using the intermediate, hydrazine hydrate and an organic acid with an R-COOH structure. The dihydropyrazole MurA enzyme inhibitor molecule provided by the invention has a bacterial inhibition effect, has an MurA enzyme inhibition effect, and also has an effect of interfering synthesis of bacterial cell walls.
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Paragraph 0068-0073
(2021/05/12)
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- Synthetic method for portulacanone compounds and their derivatives and anti-inflammatory pharmaceutical compounds containing thereof
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The present inventors synthesized described portulacanone derivatives (compound 1: R^1, R^2 = H; and compound 2: R^1, R^2 = H), natural homoisoflavonoids (andplusmn;)-portulacanone A-C (compound 4: R^1 = OMe, R^2 = H; compound 8: R^1, R^2 = OMe; and compound 9: R^1 = OH, R^2 = OMe), and derivatives thereof (compound 3: R^1 = OMe, R^2 = H; compound 5: R^1 = OH, R^2 = H, and compound 7: R^1, R^2 = OMe), and thus evaluated ability to inhibit NO production in LPS-induced RAW 264.7 macrophages as an indicator of anti-inflammatory activity. All tested compounds showed no clear cytotoxicity and inhibited NO production in a concentration dependent manner in RAW 264.7 macrophages. A compound 3 (97.2% inhibition at 10 andmu;M; IC50 = 1.26 andmu;M) shows a significant inhibition effect compared to a compound 1 (91.4% inhibition at 10 andmu;M; IC50 = 1.75 andmu;M) and a compound 7 (83.0% inhibition at 10 andmu;M; IC50 = 2.91 andmu;M). Compounds of the present invention are useful for developing NO producing targeted anti-inflammatory drugs.COPYRIGHT KIPO 2019
- -
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Paragraph 0088; 0094; 0095
(2019/09/05)
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- Synthetic method for portulacanone D and anti-inflammatory pharmaceutical compounds containing thereof
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Inventors of the present invention synthesized natural homoisoflavonoid portulacanone D (compound 6) isolated from Portulaca oleracea L (POL). An ability to inhibit NO production in LPS-induced RAW 264.7 macrophages was assessed as an indicator of anti-inflammatory activity. The tested portulacanone D did not show clear cytotoxicity and inhibited NO production in the RAW 264.7 macrophages in a concentration dependent manner. The portulacanone D exhibits 92.5% of NO production inhibition at 10 andmu;M and has an IC50 value of 2.09 andmu;M. The finding has additional correlation with the suppressed expression of iNOS induced by LPS. According to the information obtained from the study of the present invention, the portulacanone D can be used in the development of anti-inflammatory drugs targeting NO production.COPYRIGHT KIPO 2019
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Paragraph 0060; 0061
(2019/10/08)
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- The winding road of the uvaretin class of natural products: From total synthesis to bioactive agent discovery
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Herein, we disclose the development of a synthetic route to gain access to the uvaretin class of chalcone natural products. In this, the construction of a small library was achieved, and the collection was evaluated for cytotoxicity and other biological properties. Uvaretin (1) was accessed via a seven-step route in an overall yield of 15.1%. Within this route, the unsaturated enone variant of uvaretin (2), also a natural product, was accessed in a 16.7% yield over six steps. This route provides a nearly three-fold increase in yields of 1 and 2 in comparison to the previous synthetic route accessing them in 5.8% and 3.0% overall yields, respectively. Evaluation of 1 and 2 revealed IC50 values between 2.0 and 5.1 μM in the cancerous cell lines HeLa, U937, A549, and MIA PaCa-2. Screening of the whole chalcone library set led to the discovery of over 30 compounds, within six cancerous cell lines, possessing single digit μM IC50 activity as sole agents. Furthermore, multiple library members were found to possess promising potentiating properties with known chemotherapeutic agents.
- Dallman, Johnathan,Lansakara, Ashabha,Nguyen, Thi,Weeramange, Chamitha,Hulangamuwa, Wasundara,Rafferty, Ryan J.
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p. 1420 - 1431
(2019/08/21)
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- Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream
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We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.
- Liu, Guangchang,Xu, Bo
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supporting information
p. 869 - 872
(2018/02/09)
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- Synthesis and in vitro evaluation of homoisoflavonoids as potent inhibitors of nitric oxide production in RAW-264.7 cells
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Syntheses of natural homoisoflavonoids, (±)-portulacanones A–C (4, 8 and 9), portulacanone D (6), isolated from Portulaca oleracea L. (POL) and their derivatives (3, 5 and 7) have been achieved for the first time along with the synthesis of known derivatives (1 and 2) and their in vitro inhibitory effect against NO production in LPS-induced RAW-264.7 macrophages was evaluated as an indicator of anti-inflammatory activity. All the compounds tested had a concentration-dependent inhibitory effect on NO production by RAW-264.7 macrophages without obvious cytotoxicity. Compounds 3 (97.2% at 10 μM; IC50 = 1.26 μM) followed by 6 (portulacanone D) (92.5% at 10 μM; IC50 = 2.09 μM), 1 (91.4% at 10 μM; IC50 = 1.75 μM) and 7 (83.0% at 10 μM; IC50 = 2.91 μM) were the most potent from the series. This finding was further correlated with the suppressed expression of iNOS induced by LPS. Our promising preliminary results may provide the basis for the assessment of compound 3 as a lead structure for a NO production-targeted anti-inflammatory drug development and also could support the usefulness of POL as a folklore medicinal plant in the treatment of inflammatory diseases.
- Damodar, Kongara,Lee, Jeong Tae,Kim, Jin-Kyung,Jun, Jong-Gab
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supporting information
p. 2098 - 2102
(2018/04/30)
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- Novel neohesperidin dihydrochalcone analogue inhibits adipogenic differentiation of human adipose-derived stem cells through the Nrf2 pathway
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Obesity, characterized by excess lipid accumulation, has emerged as a leading public health problem. Excessive, adipocyte-induced lipid accumulation raises the risk of metabolic disorders. Adipose-derived stem cells (ASCs) are mesenchymal stem cells (MSCs
- Han, Ga Eun,Kang, Hee-Taik,Chung, Sungkyun,Lim, Changjin,Linton, John A.,Lee, Jin-Hee,Kim, Wooki,Kim, Seok-Ho,Lee, Jong Hun
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- P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis
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p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.
- Pandey, Ganesh,Tiwari, Sandip Kumar,Singh, Bhawana,Vanka, Kumar,Jain, Shailja
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supporting information
p. 12337 - 12340
(2017/11/20)
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- Hexafluoro-2-propanol-Promoted Intermolecular Friedel-Crafts Acylation Reaction
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The intermolecular Friedel-Crafts acylation was carried out in hexafluoro-2-propanol to yield aryl and heteroaryl ketones at room temperature without any additional reagents.
- Vekariya, Rakesh H.,Aubé, Jeffrey
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supporting information
p. 3534 - 3537
(2016/08/16)
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- Metal Sulfonate Polymers as Catalysts for the Heterogeneous Acylation of Aromatic Derivatives
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A series of metal sulfonate salts attached to a poly(ether ether ketone) (PEEK) polymer were prepared by ultrasonic activation and then examined as heterogeneous catalysts in the Friedel–Crafts acylation of aromatic derivatives.
- Morizur, Vincent,Hector, Daphné,Olivero, Sandra,Desmurs, Jean Roger,Du?ach, Elisabet
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supporting information
p. 3126 - 3129
(2016/07/12)
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- Catalysis of the acylation of aromatic derivatives by metallic tosylates
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A series of metallic tosylates were prepared by ultrasonic metal activation and were further used as efficient catalysts for the acylation of aromatic derivatives.
- Morizur, Vincent,Szafranek, Jessica,Bonhomme, Dominique,Olivero, Sandra,Desmurs, Jean Roger,Du?ach, Elisabet
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supporting information
p. 6813 - 6817
(2015/08/24)
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- Design, synthesis, characterization and in vitro and in vivo anti-inflammatory evaluation of novel pyrazole-based chalcones
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A series of novel pyrazole-based chalcones have been designed, synthesized from 1-methyl-5-(2,4,6-trimethoxyphenyl)-1H-pyrazole (6). The structures of regioisomers 6 and 7 were determined by 2D 1H-1H COSY, 1H-13C HSQC and 1H-13C HMBC experiments. The newly synthesized compounds were tested for their inhibitory activity against COX-1 and COX-2 using an in vitro cyclooxygenase (COX) inhibition assay. Moreover, they were investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw edema model for acute inflammation and cotton pellet-induced granuloma model for chronic inflammation. All the synthesized compounds showed potential to demonstrate anti-inflammatory activities, of particular interest compounds 10i, 10e , 10f, and 10h were found to be potent anti-inflammatory agents.
- Chavan, Hemant V.,Adsul, Laxman K.,Kotmale, Amol S.,Dhakane, Valmik D.,Thakare, Vishnu N.,Bandgar, Babasaheb P.
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-
- Synthesis of xanthohumol analogues and discovery of potent thioredoxin reductase inhibitor as potential anticancer agent
-
The selenoprotein thioredoxin reductases (TrxRs) are attractive targets for anticancer drugs development. Xanthohumol (Xn), a naturally occurring polyphenol chalcone from hops, has received increasing attention because of its multiple pharmacological activities. We synthesized Xn and its 43 analogues and discovered that compound 13n displayed the highest cytotoxicity toward HeLa cells (IC50 = 1.4 μM). Structure-activity relationship study indicates that the prenyl group is not necessary for cytotoxicity, and introducing electron-withdrawing group, especially on the meta-position, is favored. In addition, methylation of the phenoxyl groups generally improves the potency. Mechanistic study revealed that 13n selectively inhibits TrxR and induces reactive oxygen species and apoptosis in HeLa cells. Cells overexpressing TrxR are resistant to 13n insult, while knockdown of TrxR sensitizes cells to 13n treatment, highlighting the physiological significance of targeting TrxR by 13n. The clarification of the structural determinants for the potency would guide the design of novel potent molecules for future development.
- Zhang, Baoxin,Duan, Dongzhu,Ge, Chunpo,Yao, Juan,Liu, Yaping,Li, Xinming,Fang, Jianguo
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supporting information
p. 1795 - 1805
(2015/04/27)
-
- Total synthesis of luteolin
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Luteolin is a naturally-occurring polyphenolic flavonoid compound which has received considerable attention because of its wide range of biological and pharmacological properties. Efficient methods are reported for preparing luteolin, based on the acylation of 1,3,5-trimethoxybenzene and condensation with 3,4-dimethoxybenzaldehyde or the reaction of 3,4-dimethoxycinnamic acid with 1,3,5-trimethoxybenzene. The first of these is the better method.
- Zhang, Ji,Liu, Man,Cui, Wei,Yang, Jian,Yang, Bo
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- An efficient synthesis of chrysin
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Two routes for the synthesis of the flavones chrysin are described. In the first 1,3,5-trimethoxybenzene was converted to 2-hydroxy-4,6- dimethoxyacetophenone and then by condensation with benzaldehyde to 2′-hydroxy-4′,6′-dimethoxychalcone. The latter was cyclised with iodine and demethylated with pyridine hydrochloride to form chrysin in 53% overall yield. In the second route, 1,3,5-trimethoxybenzene was acylated with cinnamic acid to form the chalcone which was then converted to chrysin in 30.7% overall yield.
- Liu, Man,Zhang, Ji,Yang, Jian,Yang, Bo,Cui, Wei
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p. 134 - 136
(2014/04/17)
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- A novel synthesis of naringenin and related flavanones
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Efficient methods are reported for the preparation of naringenin (4',5,7-trihydroxyflavanone) which could be easily scaled-up. They have been applied to three other flavanones (6.hydroxyflavanone, 6,4'-dihydroxyflavanone, 6,3',4'-trihydroxyflavanone) suitably.
- Cui, Wei,Zhang, Ji,Wang, Qian,Gao, Kai,Zhang, Wei,Yang, Jian
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p. 686 - 689
(2015/02/19)
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- Efficient and recyclable rare earth-based catalysts for Friedel-Crafts acylations under microwave heating: Dendrimers show the way
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The catalytic system involving Sc(OTf)3 and a dendritic terpyridine ligand is able to promote the Friedel-Crafts acylation of a wide range of aromatics under microwave irradiation. The expected products are obtained in high yields after short reaction times and the nano-sized catalyst can be recovered and successfully used in 12 consecutive runs.
- Perrier, Arnaud,Keller, Michel,Caminade, Anne-Marie,Majoral, Jean-Pierre,Ouali, Armelle
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supporting information
p. 2075 - 2080
(2013/09/24)
-
- Total syntheses of norartocarpin and artocarpin
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The total syntheses of norartocarpin and artocarpin, two biologically interesting natural flavonoids with two regioisomeric isoprenyl side chains, were achieved for the first time via a linear reaction sequence of 9 and 12 steps with the overall yields of
- Zhang, Wen-Jing,Wu, Jing-Fang,Zhou, Peng-Fei,Wang, Yang,Hou, Ai-Jun
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p. 5850 - 5858
(2013/07/27)
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- Design, synthesis, characterization and biological evaluation of novel pyrazole integrated benzophenones
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A series of novel pyrazole integrated benzophenones (9a-j) have been designed, synthesized from 1-methyl-5-(2,4,6-trimethoxy-phenyl)-1H-pyrazole 6. The structures of the regioisomers 6 and 7 were determined by 2D 1H-1H COSY, 1H-13C HSQC and 1H-13C HMBC experiments. The newly synthesized compounds (9a-j) were evaluated for in vivo anti-inflammatory activity by carrageenan paw edema in rats and in vitro COX-1/COX-2 inhibition and antioxidant potential. Among the synthesized compounds, compounds 9b, 9d and 9f, were found to be active anti-inflammatory agents in addition to having potent antioxidant activity.
- Bandgar, Babasaheb P.,Chavan, Hemant V.,Adsul, Laxman K.,Thakare, Vishnu N.,Shringare, Sadanand N.,Shaikh, Rafik,Gacche, Rajesh N.
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p. 912 - 916
(2013/02/25)
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- Design, synthesis, characterization and anti-inflammatory evaluation of novel pyrazole amalgamated flavones
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A series of novel pyrazole amalgamated flavones has been designed and synthesized from 1-methyl-5-(2,4,6-trimethoxy-phenyl)-1H-pyrazole 6. The structures of regioisomers 6 and 7 were resolved by 2D 1H- 1H COSY, 1H-13C HSQC and 1H- 13C HMBC experiments. The newly synthesized compounds were tested for their in vitro COX inhibition and in vivo carrageenan induced hind paw edema in rats and acetic acid induced vascular permeability in mice. Although the compounds have inhibitory profile against both COX-1 and COX-2, some of the compounds are found to be selective against COX-2, supported by inhibition of paw edema and vascular permeability. Docking studies were also carried out to determine the structural features which sway the anti-inflammatory activity of the tested compounds. The keto and phenolic -OH are major factors that are prominently involved in interaction with COX-2 active site.
- Chavan, Hemant V.,Bandgar, Babasaheb P.,Adsul, Laxman K.,Dhakane, Valmik D.,Bhale, Pravin S.,Thakare, Vishnu N.,Masand, Vijay
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p. 1315 - 1321
(2013/03/14)
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- Trimethoxy-chalcone derivatives inhibit growth of Leishmania braziliensis: Synthesis, biological evaluation, molecular modeling and structure-activity relationship (SAR)
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In this work we described the synthesis, the antileishmanial activity and the molecular modeling and structure-activity relationship (SAR) evaluations of a series of chalcone derivatives. Among these compounds, the methoxychalcones 2h, 2i, 2j, 2k and 2l showed significant antileishmanial activity (IC 50 50 = 2.7 μM), 2j (IC50 = 3.9 μM) and 2k (IC50 = 4.6 μM) derivatives presented better antileishmanial activity than the control drug pentamidine (IC50 = 6.0 μM). Our SAR study showed the importance of methoxy di-ortho substitution at phenyl ring A and the relationship between the frontier orbital HOMO coefficients distribution of these molecules and their activity. The most active compounds 2h, 2i, 2j, 2k, and 2l fulfilled the Lipinski rule-of-five which theoretically is important for good drug absorption and permeation through biological membranes. The potential profile of 2j (IC 50 = 3.9 μM and CC50 = 216 μM) pointed this chalcone derivative as a hit compound to be further explored in antileishmanial drug design.
- Bello, Murilo Lamim,Chiaradia, Louise Domeneghini,Dias, Luiza Rosaria Sousa,Pacheco, Leticia Kramer,Stumpf, Taisa Regina,Mascarello, Alessandra,Steindel, Mario,Yunes, Rosendo Augusto,Castro, Helena Carla,Nunes, Ricardo Jose,Rodrigues, Carlos Rangel
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p. 5046 - 5052
(2011/09/30)
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- Synthesis of aryl ketones by palladium(II)-catalyzed decarboxylative addition of benzoic acids to nitriles
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An efficient, sustainable method for the preparation of aryl ketones from ortho-substituted benzoic acids proceeds through their decarboxylation to generate an aryl-palladium species, followed by addition to a nitrile and hydrolysis of the intermediate ketimine.
- Lindh, Jonas,Sjoeberg, Per J. R.,Larhed, Mats
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supporting information; experimental part
p. 7733 - 7737
(2011/01/05)
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- Total synthesis of 3′,3?-binaringenin and related biflavonoids
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The synthesis of natural 3++,3?-binaringenin and four related biflavonoids was performed in good overall yield (15-35%) starting from readily available phloroglucinol and 4-hydroxy- or 4-methoxybenzaldehyde. Preliminary results indicate that some of these compounds have an interesting activity against S. aureus. Georg Thieme Verlag Stuttgart.
- Sagrera, Gabriel,Seoane, Gustavo
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scheme or table
p. 2776 - 2786
(2010/10/19)
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- Studies towards the stereoselective α-hydroxylation of flavanones. Biosynthetic significance
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The enolates of various propiophenones, chromanones, and also analogues of naturally occurring flavanones were stereoselectively hydroxylated at the ?-position, by employing commercially available enantiopure oxaziridines, to afford the desired ?-hydroxylated target molecules in good to exceptional stereoselectivities and in moderate to good chemical yields. A mechanistic rationale is presented to account for the stereoselectivities achieved. These in vitro results were tentatively related to the stereoselective biosynthesis of enantio-enriched dihydroflavonols while questions were raised about the authenticity of certain natural compounds. CSIRO 2008.
- Border, Zola-Michele,Marais, Charlene,Bezuidenhoudt, Barend C. B.,Steenkamp, Jacobus A.
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p. 122 - 130
(2008/04/11)
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- Synthesis and pharmacological activity of chalcones derived from 2,4,6-trimethoxyacetophenone in RAW 264.7 cells stimulated by LPS: Quantitative structure-activity relationships
-
Inhibition of nitric oxide (NO) production by altering the expression of induced enzymes involved is potentially an important strategy for obtaining antiinflammatory agents. In the search for hits to obtain lead compounds for new drugs of this class, 14 s
- Chiaradia, Louise Domeneghini,dos Santos, Rodrigo,Vitor, Carlos Eduardo,Vieira, Andre Alexandre,Leal, Paulo Cesar,Nunes, Ricardo Jose,Calixto, Joao Batista,Yunes, Rosendo Augusto
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p. 658 - 667
(2008/09/17)
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- Miscrowave-assisted efficient synthesis of polymethoxyacetophenones and natural polymethoxyflavones, and thier inhibitory effects on melanogenesis
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Microwave, assisted Friedel-Crafts acetylation of polymethoxybenzenes with acetic anhydride in the presence of In(CF3SO3)3 under solvent-free conditions was achieved rapidly to give polymethoxyacetophenones in high yields. Microwave-assisted benzoylation of 2'-hydroxypolymethoxyacetophenones with polymethoxybenzoyl chlorides, followed by the rearrangement of the resulting benzoates and the final formation of natural polymethoxyflavones was achieved rapidly and efficiently. The polymethoxyflavones showed inhibitory effects on melanogenesis in human melanoma cells.
- Tsukayama, Masao,Kusunoki, Eiji,Hossain, Mohammad M.,Kawamura, Yasuhiko,Hayashi, Shinji
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p. 1589 - 1600
(2008/09/17)
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- A "Hard/Soft" Mismatch Enables Catalytic Friedel-Crafts Acylations
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(Equation Presented) Cationic complexes of Pt(II) and other late transition metals efficiently catalyze Friedel-Crafts acylations of moderately activated arenes by carboxylic acid anhydrides. The nature of the catalytically relevant species formed from (PhCN)2PtCl2 and AgSbF6 and their interactions with the substrates are studied by NMR and ESI-MS.
- Fuerstner, Alois,Voigtlaender, David,Schrader, Wolfgang,Giebel, Dirk,Reetz, Manfred T.
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p. 417 - 420
(2007/10/03)
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- Total synthesis of kaempferol and methylated kaempferol derivatives
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Kaempferol (1), a natural product from various plants, was synthesized in which the longest linear sequence is only seven steps in overall yields of 47% from commercially available 1,3,5-trimethoxybenzene (10). The methylated kaempferols 2-5 were also prepared by use of this concise synthetic methodology. The key transformations in this synthesis involved the I2 oxidative-promoting-cyclization and DDO oxidative hydroxylation. Several strategies to achieve 1 are provided.
- Lee, Yean-Jang,Wu, Tsao-Dong
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p. 201 - 206
(2007/10/03)
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- Synthesis of maritimin, a chromone from Pancratium maritimum
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The synthesis of maritimin (1), a chromone from Pancratium maritimum L., is described.
- Asolkar, Ratnakar N.,Kamat, Vijayendra P.,Kirtany, Janardan K.
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p. 549 - 550
(2007/10/03)
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- Some unusual observations in the synthesis of benzofuran based nor-neolignan
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Extension of the copper acetylide route to the 2-arylbenzofuran 1 having 2,4-6-oxygenation pattern in the side phenyl ring has led to some unusual observations finally resulting in 8.
- Panda,Parthasarathy
-
p. 628 - 631
(2007/10/03)
-
- Chameleon catches in combinatorial chemistry: Tebbe olefination of polymer supported esters and the synthesis of amines, cyclohexanones, enones, methyl ketones and thiazoles
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Tebbe olefination of supported esters R1CO2CH2-polymer gave the corresponding vinyl ethers R1C(=CH2)OCH2-polymer which were released, under acidic conditions, to produce methyl ketones R1COMe; by reductive amination, to produce amines R1CH(Me)NHR2; by bromination and reaction of R1CBr(CH2Br)OCH2-polymer with thioureas to produce thiazoles; or, for supported dienyl ethers derived from α,β-unsaturated esters, by Diels-Alder reaction and acid mediated cleavage to produce cyclohexanone derivatives.
- Ball, Christopher P.,Barrett, Anthony G. M.,Commercon, Alain,Compere, Delphine,Kuhn, Cyrille,Roberts, Richard S.,Smith, Marie L.,Venier, Olivier
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p. 2019 - 2020
(2007/10/03)
-
- Antispasmodic activity of xanthoxyline derivatives: Structure-activity relationships
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The antispasmodic activity of several xanthoxyline derivatives against acetylcholine-induced contraction of the guinea pig ileum was evaluated in vitro. The acetophenones with two methoxyl groups, mainly in the 3,4 positions, exhibited potent antispasmodic activity. Modification of the hydroxyl group in xanthoxyline by the introduction of benzoyl, acetyl, or tosyl groups produced inactive compounds, whereas the introduction of benzyl or p-methoxybenzyl groups furnished compounds that were four- to eight-fold more potent than xanthoxyline. In marked contrast, the introduction of a methyl group gave a compound that caused contractant activity. Modification of the carbonyl group of xanthoxyline lead to inactive compounds, whereas the condensation of xanthoxyline with benzaldehydes gave chalkones that were about fivefold more potent than xanthoxyline. The introduction of benzyl and styrene groups, on the basis of the similarity with papaverine, improves the antispasmodic action of the xanthoxyline derivatives. Our results suggest that the methoxyl and carbonyl groups are critical structural points for the antispasmodic activity of xanthoxyline derivatives. The hydroxyl group improves antispasmodic activity, but is not fundamental to its manifestation.
- Filho,Miguel,Nunes,Calixto,Yunes
-
p. 473 - 475
(2007/10/02)
-
- Chlorosulfination with Thionyl Chloride of Aromatic Methyl Ethers Containing Other Functional Groups
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Further studies on the direct chlorosulfination with thionyl chloride of aroamtic methyl ethers are described.In some cases (e.g. 1,6-dimethoxynaphthalene, 1,2,4-trimethoxybenzene, ethyl 3,5- and 3,7-dimethoxy-2-naphthoate, 3,5-dimethoxyphenyl benzoate) g
- Bell, Kevin H.,McCaffery, Leslie F.
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p. 1213 - 1224
(2007/10/02)
-
- FREE AND GLUCOSYLOXY ACETOPHENONES FROM PANCRATIUM BIFLORUM
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Two new dimethoxy-acetophenone-O-glucosides and the known 2,4,6-trimethoxyacetophenone were isolated from the flowering bulbs and pseudo-stem fluid of Pancratium biflorum.The structures of the new compounds were established as 4,6-dimethoxyacetophenone-2-O-β-D-glucoside and 2,6-dimethoxyacetophenone-4-O-β-D-glucoside on the basis of chemical transformation, comprehensive spectroscopic analyses, and synthesis of the aglucones.The biological activity profile of the glucosides and their aglucones is also appraised. Key Word Index Pancratium biflorum; Amaryllidaceae; flowering bulbs; pseudo-stem fluid; dimethoxy acetophenones; dimethoxy acetophenone-O-glucosides; effects on cell growth, viability; prostaglandin synthetase inhibitor.
- Ghosal, Shibnath,Mittal, Peeyush,Kumar, Yatendra,Singh, Sushil, K.
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p. 3193 - 3196
(2007/10/02)
-
- The Chemistry of Nitrilium Salts. Part 1. Acylation of Phenols and Phenol Ethers with Nitriles and Trifluoromethanesulphonic Acid
-
Aliphatic nitriles, RCN (R = Me, n-Pr, CH2Cl, and CCl3), in the presence of trifluoromethanesulphonic acid have been found to react with a number of mono-, di-, and tri-substituted phenols and phenol ethers at room temperature to give ketones after hydrolysis of the reaction mixture.Moderate to good yields of acylation products are obtained in the majority of these reactions.The yield with malononitrile and succinonitrile, which are only slightly soluble in the reaction medium, are generally poor, and reaction involves only one of the available nitrile groups.Attempts to use diethyl ether and dichloromethane as solvents for some of these reactions were unsuccessful, but limited success was achieved with nitromethane.
- Booth, Brian L.,Noori, Ghazi F.M.
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p. 2894 - 2900
(2007/10/02)
-