cas 31165-67-0, 2'-BENZYLOXYACETOPHENONE | Articles data

Articles about 31165-67-0Total 41 be found

Article title
Article abstract
Author
Journal number and time
Download

Conformational analysis: 3JHCOC and 3JHCCC Karplus relationships for methylene 1H nuclei
NAMFIS (NMR Analysis of Molecular Flexibility In Solution) was applied to 1-[2-(benzyloxy)phenyl]ethanone using quantitative 1H-1H NOE distances and 3J proton-carbon coupling constant (CC) restraints for averaged methylene
Grimmer, Craig D.,Slabber, Cathryn A.
p. 590 - 595
(2015)
Read Online

Method for synthesizing aryl benzyl ether compound
The invention discloses a method for synthesizing aryl benzyl ether compounds, which comprises the following steps: by using an iron (III) complex containing 1, 3-di-tert-butyl imidazole cations and having a molecular formula of [(tBuNCH = CHNtBu) CH] [FeBr4] as a catalyst and di-tert-butyl peroxide as an oxidant, carrying out oxidative coupling reaction on phenolic compounds and toluene compounds to synthesize the corresponding aryl benzyl ether compounds. The method is the first example for preparing the aryl benzyl ether compound through the oxidative coupling reaction of the phenolic compound and the toluene compound, which is realized by an iron-based catalyst, and has the advantages of atom economy, environmental friendliness and good substrate applicability.
-
Paragraph 0027; 0041

(2021/04/14)

Application of iron (III) complex containing 1,3-di-tert-butyl imidazole cations in synthesis of aryl benzyl ether compounds
The invention discloses an application of an iron (III) complex containing 1,3-di-tert-butyl imidazole cations in synthesis of aryl benzyl ether compounds, and particularly relates to a method for synthesizing corresponding aryl benzyl ether compounds by taking di-tert-butyl peroxide as an oxidizing agent and carrying out oxidative coupling reaction on phenolic compounds and toluene compounds. According to the method, the iron (III) complex is used as the catalyst for the first time, and oxidative coupling of the phenolic compound and the toluene compound is realized. The method is the first oxidative coupling reaction of phenolic compounds and benzyl C(sp3)-H bonds, and a new method is provided for synthesizing aryl benzyl ether compounds. Compared with an existing synthesis method, the method provided by the invention avoids using toxic and polluting halogenated hydrocarbon and strong base, has better atom economy, and conforms to the development concept of green synthetic chemistry.
-
Paragraph 0026-0027

(2021/04/26)

Design, synthesis and biological activity of selective hCAs inhibitors based on 2-(benzylsulfinyl)benzoic acid scaffold
A large library of derivatives based on the scaffold of 2-(benzylsulfinyl)benzoic acid were synthesised and tested as atypical inhibitors against four different isoforms of human carbonic anhydrase (hCA I, II, IX and XII, EC 4.2.1.1). The exploration of the chemical space around the main functional groups led to the discovery of selective hCA IX inhibitors in the micromolar/nanomolar range, thus establishing robust structure-activity relationships within this versatile scaffold. HPLC separation of some selected chiral compounds and biological evaluation of the corresponding enantiomers was performed along with molecular modelling studies on the most active derivatives.
Rotondi, Giulia,Guglielmi, Paolo,Carradori, Simone,Secci, Daniela,De Monte, Celeste,De Filippis, Barbara,Maccallini, Cristina,Amoroso, Rosa,Cirilli, Roberto,Akdemir, Atilla,Angeli, Andrea,Supuran, Claudiu T.
p. 1400 - 1413
(2019/08/26)

Design, synthesis and biological evaluation of novel ring-opened cromakalim analogues with relaxant effects on vascular and respiratory smooth muscles and as stimulators of elastin synthesis
Two new series of ring-opened analogues of cromakalim bearing sulfonylurea moieties (series A: with N-unmethylated sulfonylureas, series B: with N-methylated sulfonylureas) were synthesized and tested as relaxants of vascular and respiratory smooth muscle
Bouhedja, Mourad,Peres, Basile,Fhayli, Wassim,Ghandour, Zeinab,Boumendjel, Ahcène,Faury, Gilles,Khelili, Smail
p. 774 - 796
(2018/01/05)

Synthesis of Spirofurooxindoles via Phenyliodine(III) Bis(trifluoroacetate) (PIFA)-Mediated Cascade Oxidative C?O and C?C Bond Formation
Upon treatment with solely a hypervalent iodine reagent of phenyliodine(III) bis(trifluoroacetate) (PIFA), 3-(2-hydroxyphenyl)-3-oxo-N-phenyl propanamides and a series of its derivatives were conveniently converted to a class of undocumented spirofurooxindoles under mild conditions. Control experiments provided evidence that this spirocyclization process encompassed a cascade oxidative reactions involving the formation of a C?O bond prior to that of C?C bond. (Figure presented.).
Sun, Desong,Zhao, Xiaoyuan,Zhang, Bobo,Cong, Ying,Wan, Xintong,Bao, Mingmai,Zhao, Xue,Li, Bing,Zhang-Negrerie, Daisy,Du, Yunfei
supporting information
p. 1634 - 1638
(2018/03/21)

C-H Functionalization via Remote Hydride Elimination: Palladium Catalyzed Dehydrogenation of ortho-Acyl Phenols to Flavonoids
Although deprotonation of electron-poor C-H bonds to carbon anions with bases has long been known and widely used in organic synthesis, the hydride elimination from electron-rich C-H bonds to carbon cations or partial carbocations for the introduction of nucleophiles is a comparatively less explored area. Here we report that the carbonyl β-C(sp3)-H bond hydrogens of ortho-acyl phenols could be substituted by intramolecular phenolic hydroxyls to form O-heterocycles, followed by dehydrogenation of the O-heterocycle into flavonoids. The cascade reaction is catalyzed by Pd/C without added oxidants and sacrificing hydrogen acceptors.
Zhao, Xiaomei,Zhou, Jiabin,Lin, Shuying,Jin, Xukang,Liu, Renhua
supporting information
p. 976 - 979
(2017/03/14)

COMPOSITIONS AND METHODS OF REGULATING CANCER RELATED DISORDERS AND DISEASES
Provided herein are naphthylic derivative compounds, or pharmaceutically acceptable salts thereof, that are useful for inhibiting cancers. Also provided herein are methods of using effective amounts of said compounds, optionally with pharmaceutical carrie
-
Paragraph 135

(2017/08/01)

Synthesis of Benzofurans from Ketones and 1,4-Benzoquinones
Benzofuran derivatives can be synthesized through the sequential Michael addition and cyclization of 1,3-dicarbonyl compounds with 1,4-benzoquinones. However, ketones are rarely used in this reaction because of their low nucleophilicities. In this study, this problem was solved by utilizing triethyl orthoformate, which enabled the formation of a vinyl ethyl ether as an additive. As a result, the nucleophilicity of ketones increased. Many important 5-hydroxybenzofuran derivatives, which were not readily available by synthesis in the past, were also prepared via these newly established reactions. (Figure presented.) .
Wu, Fengtian,Bai, Rongxian,Gu, Yanlong
p. 2307 - 2316
(2016/07/29)

Multifunctional heterocyclic scaffolds for hybrid Lewis acid/Lewis base catalysis of carbon–carbon bond formation
Several new classes of hybrid catalysts have been synthesized by tethering heterocyclic metal (Lewis acid) chelating scaffolds to several different amines capable of facilitating enamine catalysis. Oxazole, thiazole, and imidazole-based chiral precatalyst
Wiedenhoeft, Dennis,Benoit, Adam R.,Wu, Yibiao,Porter, Jacob D.,Meyle, Elisia,Yeung, Teresa H.W.,Huff, Raechel,Lindeman, Sergey V.,Dockendorff, Chris
p. 3905 - 3916
(2016/07/06)

Pd(OAc)2/S=PPh3 accelerated activation of gem-dichloroalkenes for the construction of 3-arylchromones
The Pd-catalyzed regioselective intramolecular nucleophilic substitution of gem-dichloroalkene derivatives with salicylaldehydes leading to the synthesis of 3-arylchromones has been developed. Pd(OAc)2/S=PPh3 could activate gem-dichloroalkenes and undergo nucleophilic substitution by salicylaldehydes with the aid of a base.
Liu, Jianming,Song, Weiwei,Yue, Yuanyuan,Liu, Ren,Yi, Hong,Zhuo, Kelei,Lei, Aiwen
supporting information
p. 17576 - 17579
(2015/12/08)

Natural Products as Sources of New Fungicides (I): Synthesis and Antifungal Activity of Acetophenone Derivatives Against Phytopathogenic Fungi
Several series of 45 acetophenone derivatives bearing various alkyl or benzyl substituents were conveniently synthesized and their structures characterized by 1H and 13C NMR spectroscopy, HRMS and single-crystal X-ray analysis. Their in vitro antifungal activities against a panel of phytopathogenic fungi were evaluated by mycelial growth rate assay. Of them, 12 derivatives (e.g., 3a-c, 4c and 4e) exhibited more potent antifungal effects on some phytopathogens than a commercial fungicide hymexazol as positive control. In particular, compound 3b with IC50 values of 10-19μg/mL was found to be the most active in this series and might be a potential lead structure for further optimization. The preliminary structure-activity relationship (SAR) studies of a series of acetophenones are also discussed. A series of acetophenone derivatives have been synthesized and tested for their antifungal activities. Of them 12 derivatives exhibited more potent antifungal effects on some phytopathogens than a positive control hymexazol. Especially, compound 3b (IC50=10-19μg/mL) was found to be the most active and might be a potential lead structure. The SAR of these acetophenones is also discussed.
Ma, Ya-Tuan,Fan, Hua-Fang,Gao, Yu-Qi,Li, He,Zhang, An-Ling,Gao, Jin-Ming
p. 545 - 552
(2013/06/05)

Synthesis and antifungal activities of natural and synthetic biflavonoids
The synthesis of some natural and synthetic biflavonoids was performed in good overall yields starting from readily available materials via high yielding aldol and Ullmann condensations. Some of these compounds, especially bichalcones, display an interesting activity against fungi, higher than that of the corresponding monomers.
Sagrera, Gabriel,Bertucci, Ana,Vazquez, Alvaro,Seoane, Gustavo
experimental part
p. 3060 - 3073
(2011/06/27)

Synthesis of fluorine-containing 3-hydroxyflavanones and isoflavones
Fluorine-containing 3-hydroxyflavanones and isoflavones were synthesized by epoxidation of F-containing chalcones by hydrogen peroxide under basic conditions and subsequent intramolecular cyclization of the resulting epoxides using BF3·Et2O. The ratio of products depended on the presence and position of the F atom.
Khlebnikova,Piven,Khripach,Lakhvich
experimental part
p. 33 - 37
(2011/07/30)

Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1)
According to the structural characteristics of isoliquiritigenin from Glycyrrhiza uralensis, a series of hydroxychalcones has been designed, synthesized and evaluated for their in vitro inhibitory activities of β-secretase (BACE1). Structure-activity relationship study suggested that inhibitory activity against BACE1 was governed to a greater extent by the hydroxyl substituent on A-and B-ring of the chalcone, and the most active compound was substituted with four hydroxyl group (17, IC50=0.27 μM).
Ma, Lei,Yang, Zhengyi,Li, Chenjing,Zhu, Zhiyuan,Shen, Xu,Hu, Lihong
experimental part
p. 643 - 648
(2012/04/10)

A xanthate-based free radical approach to defucogilvocarcin M
A formal total synthesis of the aglycon of gilvocarcin M is described. The synthesis is based on the construction of the key naphthalene 7 via a free radical addition-cyclization protocol followed by aromatization of the resulting α-tetralone. This highly
Cortezano-Arellano, Omar,Cordero-Vargas, Alejandro
supporting information; experimental part
p. 602 - 604
(2010/04/05)

Counterattack mode differential acetylative deprotection of phenylmethyl ethers: Applications to solid phase organic reactions
A counterattack protocol for differential acetylative cleavage of phenylmethyl ether has been developed. The phenylmethyl moiety is liberated as benzyl bromide that is isolated and reused providing advantages in terms of waste minimization/utilization and atom economy. The applicability of this methodology has been extended for solid phase organic reactions with the feasibility of reuse of the solid support.
Chakraborti, Asit K.,Chankeshwara, Sunay V.
supporting information; experimental part
p. 1367 - 1370
(2009/07/04)

Effects of the aryl linker and the aromatic substituent on the anti-HCV activities of aryl diketoacid (ADK) analogues
Based on our pharmacophore model of the aryl diketoacids (ADKs), we designed and prepared a series of novel ADK analogues, which showed potent inhibitory activities against the NS5B polymerase in the submicromolar range. Pharmacophore-guided docking study revealed that the antiviral activities of the ADKs are highly dependent upon the aryl linker as well as the size and position of the aromatic substituent. It is of another importance that, unlike previously reported ADKs, three ADK analogues synthesized in this study effectively blocked Hepatitis C Virus (HCV) replication in the replicon systems.
Kim, Jinyoung,Kim, Ki-Sun,Lee, Hyo Seon,Park, Kwang-Su,Park, Sun Young,Kang, Seock-Yong,Lee, Soo Jae,Park, Hyung Soon,Kim, Dong-Eun,Chong, Youhoon
body text
p. 4661 - 4665
(2009/04/08)

PESTICIDAL SUBSTITUTED PHENYLETHERS
The invention relates to the use of phenylether derivatives of formula (I), to compositions thereof for the control of pests, including arthropods and helminths.
-
Page/Page column 42; 44

(2008/06/13)

THERAPEUTIC AGENT
A therapeutic agent and prophylactic agent for a disease accompanying an abnormality in an amount of insulin or insulin response, an agent for an insulin-mimetic action, a food, beverage and feed, an agent for enhancing glucose uptake into a cell, and an agent for inducing differentiation into an adipocyte, characterized in that each comprises as an effective ingredient at least one compound selected from the group consisting of a chalcone compound, an acetophenone compound, a coumarin compound, a phthalide compound, derivatives thereof, and pharmacologically acceptable salts thereof.
-
Page/Page column 65

(2010/11/08)

Synthesis and anticancer activity of benzyloxybenzaldehyde derivatives against HL-60 cells
A series of benzyloxybenzaldehyde derivatives were prepared and tested against the HL-60 cell line for anticancer activity. Preliminary structure-activity relationships were established. It was discovered that 2-(benzyloxy)benzaldehyde (17), 2-(benzyloxy)-4-methoxybenzaldehyde (26), 2-(benzyloxy)-5-methoxybenzaldehyde (27), 2-(benzyloxy)-5-chlorobenzaldehyde (28), 2-[(3-methoxybenzyl)oxy]benzaldehyde (29), 2-[(2-chlorobenzyl)oxy] benzaldehyde (30), and 2-[(4-chlorobenzyl)oxy]benzaldehyde (31) exhibited significant activity at 1-10 μM. Among them, compound 29 was the most potent one. The morphological assessment and DNA fragmentation analysis indicated that these compounds arrested cell cycle progression at G2/M phase and induced cell apoptosis. They resulted in the loss of mitochondrial membrane potential after 12 h of treatment.
Lin, Chin-Fen,Yang, Jai-Sing,Chang, Chiung-Yun,Kuo, Sheng-Chu,Lee, Miau-Rong,Huang, Li-Jiau
p. 1537 - 1544
(2007/10/03)

Synergism of low energy microwave irradiation and solid-liquid phase transfer catalysis for selective alkylation of phenols to phenolic ethers
A 100% selectivity with an order of magnitude rate enhancement is obtained in the synthesis of phenolic ethers when synergistic combination of solid-liquid phase transfer catalysis and low energy microwave irradiation (MISL-PTC) is employed. As against conventional microwave heating with 600 W power input, the current work demonstrates that a low input of 40 W leads to remarkable enhancement in rates without any destruction of the catalyst.
Yadav, Ganapati D.,Bisht, Priyal M.
p. 2885 - 2892
(2007/10/03)

Synthesis of Ether Oligomers
(Equation presented) Hydroxyaromatic aldehydes and ketones were used as building blocks to prepare ether oligomers. An iterative two-step protocol involving Mitsunobu coupling and carbonyl reduction provided a protecting-group-free route with high yields. Activity screening of an 84-member library against proteases led to the discovery of micromolar inhibitors for trypsin, chymotrypsin, and subtilisin.
Renaudet, Olivier,Reymond, Jean-Louis
p. 397 - 400
(2007/10/03)

Synthesis and structure-activity relationships of novel IKK-β inhibitors. Part 2: Improvement of in vitro activity
A series of 2-amino-3-cyano-4-alkyl-6-(2-hydroxyphenyl)pyridine derivatives was synthesized and evaluated as IκB kinase β (IKK-β) inhibitors. Substitution of an aminoalkyl group for the aromatic group at the 4-position on the core pyridine ring resulted i
Murata, Toshiki,Shimada, Mitsuyuki,Kadono, Hiroshi,Sakakibara, Sachiko,Yoshino, Takashi,Masuda, Tsutomu,Shimazaki, Makoto,Shintani, Takuya,Fuchikami, Kinji,Bacon, Kevin B.,Ziegelbauer, Karl B.,Lowinger, Timothy B.
p. 4013 - 4017
(2007/10/03)

Discovery of α,γ-Diketo Acids as Potent Selective and Reversible Inhibitors of Hepatitis C Virus NS5b RNA-Dependent RNA Polymerase
α,γ-Diketo acids (DKA) were discovered from screening as selective and reversible inhibitors of hepatitis C virus NS5b RNA-dependent RNA polymerase. The diketo acid moiety proved essential for activity, while substitution on the γ position was necessary for selectivity and potency. Optimization led to the identification of a DKA inhibitor of NS5b polymerase with IC50 = 45 nM, one of the most potent HCV NS5b polymerase inhibitors reported.
Summa, Vincenzo,Petrocchi, Alessia,Pace, Paola,Matassa, Victor G.,De Francesco, Raffaele,Altamura, Sergio,Tomei, Licia,Koch, Uwe,Neuner, Philippe
p. 14 - 17
(2007/10/03)

Synthesis and structure-activity relationships of novel IKK-β inhibitors. Part 3: Orally active anti-inflammatory agents
A series of 2-amino-3-cyano-4-alkyl-6-(2-hydroxyphenyl)pyridine derivatives was synthesized and evaluated as IκB kinase β (IKK-β) inhibitors. Modification of a novel IKK-β inhibitor 1 (IKK-β IC 50=1500nM, Cell IC50=8000nM) at the 4-p
Murata, Toshiki,Shimada, Mitsuyuki,Sakakibara, Sachiko,Yoshino, Takashi,Masuda, Tsutomu,Shintani, Takuya,Sato, Hiroki,Koriyama, Yuji,Fukushima, Keiko,Nunami, Noriko,Yamauchi, Megumi,Fuchikami, Kinji,Komura, Hiroshi,Watanabe, Akihiko,Ziegelbauer, Karl B.,Bacon, Kevin B.,Lowinger, Timothy B.
p. 4019 - 4022
(2007/10/03)

Synthesis of the Integrastatin Nucleus Using the Ramberg - Baecklund Reaction
(Equation presented) The first synthesis of the tetracyclic nucleus of the Integrastatins, natural products that have been shown to selectively inhibit HIV-1 integrase, is reported. Key steps of this synthesis involve a novel cis-selective Ramberg-Baecklund reaction and an unusual Lewis acid-promoted cyclization step.
Foot, Jonathan S.,Giblin, Gerard M. P.,Taylor, Richard J. K.
p. 4441 - 4444
(2007/10/03)

Pyridine derivatives
Pyridine compounds of general formula: wherein —R1represents in which R11is hydrogen, C1-6alkyl, halogen, hydroxy, C1-12alkoxy, nitro, amino, C1-6alkylsulfonylamino, C1-6alkoxycarbonyl, C1-6alkylamino, di(C1-6alkyl)amino, C1-6alkanoylamino, phenyl C1-6alkylamino, phenylsulfonylamino, or —O—(CH2)n—R111; R2represents hydrogen or halogen; R3represents hydrogen, —CR31R32R33, or —NR34R35; R4is hydrogen, carbamoyl, CN, carboxyl, etc.; R5is amino, C1-6alkylamino, di C1-6alkylamino, etc. or salt thereof. The compound has an excellent anti-inflammatory activity, and other biological activity.
-
(2008/06/13)

Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereoselective synthesis of Cis-disubstituted oxygen and nitrogen heterocycles
(Matrix presented) A ruthenium porphyrin-catalyzed stereoselective intramolecular carbenoid C-H insertion is described. Using [Ru II(TTP)(CO)] as catalyst, aryl tosylhydrazones are converted to 2,3-dihydrobenzofurans, 2,3-dihydroindoles, and β-lactams in good yields and remarkable cis selectivity (up to 99%). Enantioselective synthesis of 2,3-dihydrobenzofurans is also achieved with [RuII(D 4-Por*)(CO)] as catalyst, and up to 96% ee is attained.
Cheung, Wai-Hung,Zheng, Shi-Long,Yu, Wing-Yiu,Zhou, Guo-Chuan,Che, Chi-Ming
p. 2535 - 2538
(2007/10/03)

Benzyloxybenzaldehyde analogues as novel adenylyl cyclase activators
Several benzyloxybenzaldehyde analogues were prepared and found to have significant inhibitory activity toward neutrophil superoxide formation. Consequently, these compounds were evaluated for cAMP-elevating capability. Among them, benzyloxybenzaldehyde (7), exhibiting activity equivalent to forskolin, was determined as an adenylyl cyclase activator since it elevates cAMP levels by activation of adenylyl cyclase but not by inhibition of phosphodiesterase. Having a chemical structure very different from known adenylyl cyclase activators, compound 7 is recommended by us for use as a new lead compound in the future development of adenylyl cyclase activators.
Chang, Chiung-Yun,Kuo, Sheng-Chu,Lin, Yi-Lee,Wang, Jih-Pyang,Huang, Li-Jiau
p. 1971 - 1974
(2007/10/03)

Total synthesis of nominal diazonamides - Part 1: Convergent preparation of the structure proposed for (-)-diazonamide A
Unable to bear the weight of scrutiny, the original structure proposed for (-)diazonamide A (1) must be revised. A convergent, stereocontrolled total synthesis provided 1, which shows altered physical and spectroscopic characteristics relative to those of
Li, Jing,Jeong, Susan,Esser, Lothar,Harran, Patrick G.
p. 4765 - 4770
(2007/10/03)

Synthesis of 2-phenylbenzofuran derivatives as testosterone 5α- reductase inhibitor
A series of 2-phenylbenzofuran derivatives with a carbamoyl, alkylamino, or alkyloxy group at the 5 or 6 position of the benzofuran ring were synthesized and evaluated for rat and human testosterone 5α-reductase inhibitory activities in vitro. Against rat enzyme, the carbamoyl derivatives had more potent inhibitory activities than the alkylamino or alkyloxy derivatives, and the 6-carbamoyl derivatives tended to be more potent than the 5-carbamoyl derivatives. Against human enzyme, the 6-substituted derivatives had more potent inhibitory activities than the 5-substituted derivatives. The 6-carbamoyl and 6-alkylamino derivatives tended to show stronger inhibitory activities against human type 1 enzyme than against type 2 enzyme, but they were not largely selective.
Ishibashi, Koki,Nakajima, Katsuyoshi,Sugioka, Yuki,Sugiyama, Mitsuo,Hamada, Takakazu,Horikoshi, Hiroyoshi,Nishi, Takahide
p. 226 - 240
(2007/10/03)

Synthesis of fused furans by gas-phase pyrolysis of 2-allyloxyaryl-propenoic esters
Flash vacuum pyrolysis of 2-allyloxypropenoic esters (e.g. 7) gives benzo[b]furans (e.g. 32) in synthetically useful yields by sequential generation of a phenoxyl radical, cyclisation and ejection of the carboxylic ester function as a free radical leaving group. The method is compatible with a range of substituents on either the benzene ring or the propenoate chain, and is particularly effective for 2-substituted benzo[b]furans. The natural products 5-methoxybenzo[b]furan 1 and angelicin 2 have been synthesised in three and four steps respectively from commercially available starting materials by this route. Related cyclisations to give naphtho[2,1-b]furan 40 were complicated by competitive formation of naphtho[2,1-b]pyran-3-ones (e.g. 41 and 42), but the yield of the required product could be optimised by the choice of the radical precursor. Annelation of a furan ring onto a thlophene is also possible by this method, but lower yields are obtained in such pyrolyses.
Black, Michael,Cadogan,McNab, Hamish,MacPherson, Andrew D.,Roddam, V. Peter,Smith, Carol,Swenson, Helen R.
p. 2483 - 2493
(2007/10/03)

Oxygen Isosteric Derivatives of 3-(3-Hydroxyphenyl)-N-n-propylpiperidine
Some substituted 3-phenylmorpholines (10a-e,j,k) and 3-thienylmorpholines (10f,g), isosteres of 3-(3-hydroxyphenyl)-N-n-propylpiperidine (3-PPP), were prepared and submitted to binding assays on D-2 dopaminergic and 5-HT1 and 5-HT2 serotonergic receptors, in comparison with 3-PPP and its analogue 3a,b.The results show the loss of D-2 affinity for all morpholines, while a certain activity was still observable for piperidine derivatives.Regarding the serotonergic affinity, only chloro and methoxy derivatives (10a-d) were moderately active on the 5-HT1A receptor, either when the substituent was in the C-2 or C-3 position, whereas no tested compounds showed affinity toward the 5-HT2 receptor.
Perrone, Roberto,Berardi, Francesco,Leopoldo, Marcello,Tortorella, Vincenzo,Lograno, Marcello D.,et al.
p. 3045 - 3049
(2007/10/02)

Potential antitumor agents. 63. Structure-activity relationships for side-chain analogues of the colon 38 active agent 9-oxo-9H-xanthene-4-acetic acid
A series of 16 analogues of the solid tumor active compound 9-oxo-9H-xanthene-4-acetic acid (XAA), with variations in the acetic acid side chain, have been prepared and evaluated for their ability to cause early haemorrhagic necrosis of colon 38 tumors in mice. The results extend the previous SAR for this class and confirm the necessity for a carboxylic acid group in a fixed disposition with respect to the xanthenone chromophore. None of the compounds showed superior potency to XAA itself, with virtually all alterations in the nature of the anionic center or its geometry with respect to the chromophore greatly reducing or abolishing activity. However, α-methylation of the side chain was permissible, and the two enantiomers of 5-methyl-α-methyl-XAA were separated and tested. Both were active, but the S-(+) enantiomer was much more dose-potent than the R-(-) enantiomer, in both the in vivo tumor necrosis assay and an in vitro assay measuring the stimulation of nitric oxide production by macrophages. This suggests that the enantiomers have different intrinsic activities, rather than differing in their vivo metabolism.
Rewcastle,Atwell,Baguley,Boyd,Thomsen,Zhuang,Denny
p. 2864 - 2870
(2007/10/02)

Photocyclization Reactions. Part 1. Synthesis of Dihydrobenzofuranols Using Photocyclization of 2-Alkoxybenzaldehydes, 2'-Alkoxyacetophenones, 2-Formylphenoxyacetic Acids and 2-Acetylphenoxyacetic Acids
Photocyclization reactions were carried out on 2-alkoxybenzaldehydes 1a-f, 2'-alkoxyacetophenones 2a-h, 2-formylphenoxyacetic acids 1i-l and 2-acetylphenoxyacetic acids 2i-m.Irradiation opf 1a-f and 2a-h in acetonitrile gave the corresponding dihydrobenzofuranols 3, 5 and dihydroisobenzofuranols 4, 6.Using carboxylic acids 1i-l, 2i-m as starting materials, decarboxylation occurred immediately to give the corresponding ethers 1a-d, 2a-e.Further irradiation of the solution afforded dihydrobenzofuranols 3,5 and dihydroisobenzofuranols 4, 6.Substituent effects on photocyclization and reaction pathways are discussed.
Horaguchi, Takaaki,Tsukada, Chikara,Hasegawa, Eietsu,Shimizu, Takahachi,Suzuki, Tsuneo,Tanemura, Kiyoshi
p. 1261 - 1272
(2007/10/02)

The photocyclization of o-alkoxy phenyl ketones
Several o-alkoxybenzophenones and o-(benzyloxy)benzophenones and -acetophenones photocyclize to 3-hydroxy-2,3-dihydrobenzofurans. Quantum yields generally are quite high, except for o-(benzyloxy)acetophenone. The o-ethoxy and o-benzyloxy ketones form two diastereomeric products, the Z isomer being highly preferred in hydrocarbon solvents, the E isomer being formed in comparable yield in methanol or with added pyridine. The reaction involves δ-hydrogen abstraction by the ketone triplets followed by cyclization of the 1,5-biradical intermediates. The biradicals have such short lifetimes that they usually cannot be detected by flash spectroscopy or trapped by thiols. Triplet state lifetimes, determined both by steady-state quenching studies and by flash kinetics, reveal that hydrogen abstraction rate constants are quite low. Arrhenius plots for triplet decay indicate activation energies of 3-5 kcal/mol and A values of 109 for the δ-hydrogen abstraction. MMX calculations and spectroscopic data all indicate that the ketones exist primarily in conformations with the carbon α to the ether oxygen twisted well away from the carbonyl. The low observed rate constants are ascribed to even lower equilibrium populations of conformers in the geometry required for reaction in the triplet state than in the ground state. 2,6-Diacylphenyl ethers show ten times the triplet reactivity of their monoacyl equivalents. In these cases, the ether function is twisted 90° such that the target C-H bond is much closer to a carbonyl. The large solvent effects on the stereochemistry of cyclization despite short biradical lifetimes suggest that bond rotations may induce intersystem crossing of the triplet biradicals. The low cyclization quantum yield from o-(benzyloxy)acetophenone and the formation of o-benzoylacetophenone as a major side product suggest that the 1,5-biradicals partially cyclize into the benzene ring to generate spiroenol intermediates. Rate constants for quenching of the triplet ketones by 2,5-dimethyl-2,4-hexadiene were measured. The kq values are ≥5 × 109 M-1 s-1 for the o-methoxy ketones but only 1-3 × 109 for the o-benzyloxy ketones. This rare steric effect on triplet energy transfer is attributed to twisting of the benzoyl chromophores caused by steric congestion.
Wagner, Peter J.,Meador, Michael A.,Park, Bong-Ser
p. 5199 - 5211
(2007/10/02)

Synthetic aci-Reductones: 3,4-Dihydroxy-2H-1-benzopyran-2-ones and Their cis- and trans-4a,5,6,7,8,8a-Hexahydro Diastereomers. Antiaggregatory, Antilipidemic, and Redox Properties Compared to Those of the 4-Substituted 2-Hydroxytetronic Acids
Synthetic procedures for the elaboration of aci-reductones belonging to the 6- or 7-mono- or bis-substituted-3,4-dihydroxy-2H-1-benzopyran-2-ones (6 - 10) and their cis- and trans-4a,5,6,7,8,8a-hexahydro diastereomers (11, 12) are described.Hexahydrobenzo
Witiak, Donald T.,Kim, Sung K.,Tehim, Ashok K.,Sternitzke, Kent D.,McCreery, Richard L.,et al.
p. 1437 - 1445
(2007/10/02)

Synthesis of 3-Methyl-5,6-dihydro-3H-benzofuroisoquinolin-7(7aH)-ones
The coupling of 2-(alkoxymethoxy)phenylcopper derivatives with the salt of ethyl chloroformate and ethyl 3-(pyridin-3-yl)propenoate was found to be an efficient method for the preparation of 4-(2-hydroxyphenyl)pyridines 13 substituted at C-3 with a propanoate side chain.N-Methylation and O-alkylation with ethyl bromoacetate gave salts 3 which when treated with base underwent an intramolecular enolate addition to the pyridinium nucleus to produce spiro 4.Prolonged base treatment of 4 yielded ethyl 3-methyl-7-hydroxy-5,7a-dihydro-3H-benzofuroisoquinoline-6-carboxylates 5 by a Dieckmann reaction.Reduction of 5 led to predominately trans-3-methylhexahydro-1H-benzofuroisoquinolin-7(7aH)-ones, while reduction of 4 and then Dieckmann cyclization yielded mainly the cis isomers.
Weller, Dwight D.,Stirchak, Eugene P.,Weller, Doreen L.
p. 4597 - 4605
(2007/10/02)

SYNTHESIS OF 3-METHYL-2,3,4,4a,5,6-HEXAHYDRO-1H-BENZOFUROISOQUINOLINE-7(7aH)-ONES
The 2,3,4,4a,5,6-hexahydro-1H-benzofuroisoquinoline-7(7aH)-one ring system is prepared from a 4-arylpyridine precursor by sequential intramolecular enolate addition to a pyridinium ion, Dieckmann cyclization, and catalytic hydrogenation.
Weller, Dwight, D.,Weller, Doreen, L.
p. 5239 - 5242
(2007/10/02)

The Synthesis of 2-Methylchromone-3-carboxylic Acid
A new synthesis of 2-methyl-4-oxo-4H-benzopyran-3-carboxylic acid (2-methylchromone-3-carboxylic acid from salicyloyl chloride and the enamine of ethyl acetoacetate, is described and compared with the classical synthesis.
Charlton, J. L.,Lypka, G.,Sayeed, V.
p. 593 - 594
(2007/10/02)