cas 4521-28-2, 4-(4-Methoxyphenyl)butyric acid

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Pd-Catalyzed Regioselective Branched Hydrocarboxylation of Terminal Olefins with Formic Acid
A regioselective Pd-catalyzed hydrocarboxylation of terminal olefins with HCOOH is described. A wide variety of branched carboxylic acids can readily be obtained with high regioselectivities under mild reaction conditions. The reaction is operationally simple and requires no handling of toxic CO. The ligand and LiCl are important factors for reaction reactivity and selectivity.
Chu, Jianxiao,Guo, Jianqiong,Ren, Wenlong,Shi, Yian,Shi, Yuan,Wang, Mingzhou,Zhou, Jintao
supporting information
p. 886 - 891
(2022/02/07)

Identification of First-in-Class Inhibitors of Kallikrein-Related Peptidase 6 That Promote Oligodendrocyte Differentiation
Multiple sclerosis (MS) is an autoimmune demyelinating disease of the central nervous system (CNS) that causes severe motor, sensory, and cognitive impairments. Kallikrein-related peptidase (KLK)6 is the most abundant serine protease secreted in the CNS, mainly by oligodendrocytes, the myelin-producing cells of the CNS, and KLK6 is assumed to be a robust biomarker of MS, since it is highly increased in the cerebrospinal fluid (CSF) of MS patients. Here, we report the design and biological evaluation of KLK6's low-molecular-weight inhibitors, para-aminobenzyl derivatives. Interestingly, selected hit compounds were selective of the KLK6 proteolytic network encompassing KLK1 and plasmin that also participate in the development of MS physiopathology. Moreover, hits were found noncytotoxic on primary cultures of murine neurons and oligodendrocyte precursor cells (OPCs). Among them, two compounds (32 and 42) were shown to promote the differentiation of OPCs into mature oligodendrocytes in vitro constituting thus emerging leads for the development of regenerative therapies.
A?t Amiri, Sabrina,Deboux, Cyrille,Soualmia, Feryel,Chaaya, Nancy,Louet, Maxime,Duplus, Eric,Betuing, Sandrine,Nait Oumesmar, Brahim,Masurier, Nicolas,El Amri, Chahrazade
supporting information
p. 5667 - 5688
(2021/05/29)

A heavy-metal-free desulfonylative Giese-type reaction of benzothiazole sulfones under visible-light conditions
A visible-light-induced desulfonylative Giese-type reaction has been developed. Essential to the success is the employment of Hantzsch ester to activate benzothiazole sulfones without any heavy-metal additives. Not only benzylic benzothiazole sulfones but also alkyl ones were viable substrates and reacted with electron-deficient alkenes and a propiol amide.
Inuzuka, Toshiyasu,Iwama, Haruka,Ogawa, Daichi,Sengoku, Tetsuya,Yoda, Hidemi
p. 9858 - 9861
(2021/10/12)

Potential anti-neuroinflammatory NF-кB inhibitors based on 3,4-dihydronaphthalen-1(2H)-one derivatives
Nuclear factor kappa B (NF-кB) inhibition represents a new therapeutic strategy for the treatment of neuroinflammatory diseases. In this study, a series of 3,4-dihydronaphthalen-1(2H)-one (DHN; 6a-n, 7a-c) derivatives were synthesised and characterised by NMR and HRMS. We assessed the toxicity and anti-neuroinflammatory properties of these compounds and found that 6m showed the greatest anti-neuroinflammatory properties, with relatively low toxicity. Specifically, 6m significantly reduced reactive oxygen species production, down-regulated the expression of NOD-like receptor pyrin domain-containing protein 3 (NLRP3), apoptosis-associated speck-like protein containing a CARD (ASC), and caspase-1 and prevented lipopolysaccharide-stimulated BV2 microglia cells polarisation towards an M1 phenotype. Furthermore, 6m significantly decreased IκBα and NF-кB p65 phosphorylation, thus inhibiting the NF-кB signalling pathway. This suggests that 6m may be explored as a functional anti-neuroinflammatory agent for the treatment of inflammatory diseases in the central nervous system, such as multiple sclerosis, traumatic brain injury, stroke and spinal cord injury.
Sun, Yue,Zhou, Yan-Qiu,Liu, Yin-Kai,Zhang, Hong-Qin,Hou, Gui-Ge,Meng, Qing-Guo,Hou, Yun
p. 1631 - 1640
(2020/08/19)

Ligand-Controlled Regiodivergence in Nickel-Catalyzed Hydroarylation and Hydroalkenylation of Alkenyl Carboxylic Acids**
A nickel-catalyzed regiodivergent hydroarylation and hydroalkenylation of unactivated alkenyl carboxylic acids is reported, whereby the ligand environment around the metal center dictates the regiochemical outcome. Markovnikov hydrofunctionalization products are obtained under mild ligand-free conditions, with up to 99 % yield and >20:1 selectivity. Alternatively, anti-Markovnikov products can be accessed with a novel 4,4-disubstituted Pyrox ligand in excellent yield and >20:1 selectivity. Both electronic and steric effects on the ligand contribute to the high yield and selectivity. Mechanistic studies suggest a change in the turnover-limiting and selectivity-determining step induced by the optimal ligand. DFT calculations reveal that in the anti-Markovnikov pathway, repulsion between the ligand and the alkyl group is minimized (by virtue of it being 1° versus 2°) in the rate- and regioselectivity-determining transmetalation transition state.
Deng, Ruohan,Engle, Keary M.,Fu, Yue,Gao, Yang,Li, Zi-Qi,Liu, Peng,Tran, Van T.
supporting information
p. 23306 - 23312
(2020/10/19)

PROCESS FOR THE PREPARATION OF AGOMELATINE IN CRYSTALLINE FORM
The present invention pertains to a process for the preparation of polymorph form X of agomelatine, which comprises providing agomelatine, and crystallizing agomelatine in the presence of at least one of an acid and a salt thereof, and to a polymorph form of agomelatine.
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(2019/05/02)

Synthesis, crystal structures and anti-inflammatory activity of fluorine-substituted 1,4,5,6-Tetrahydrobenzo[ h]quinazolin-2-Amine derivatives
Two fluorine-substituted 1,4,5,6-Tetrahydrobenzo[h]quinazolin-2-Amine (BQA) derivatives, namely 2-Amino-4-(2-fluorophenyl)-9-methoxy-1,4,5,6-Tetrahydrobenzo[ h]quinazolin-3-ium chloride, (8), and 2-Amino-4-(4-fluorophenyl)-9-methoxy-1,4,5,6-Tetrahydrobenzo[h]quinazolin-3-ium chloride, (9), both C19H19-FN3O+-Cl-, were generated by Michael addition reactions between guanidine hydrochloride and the -,unsaturated ketones (E)-2-(2-fluorobenzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C18H15FO2, (6), and (E)-2-(4-fluorobenzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, (7). Because both sides of -,unsaturated ketones (6) or (7) can be attacked by guanidine, we obtained a pair of isomers in (8) and (9). Single-crystal X-ray diffraction indicates that each isomer has a chiral C atom and both (8) and (9) crystallize in the achiral space group P21/c. The chloride ion, as a hydrogen-bond acceptor, plays an important role in the formation of multiple hydrogen bonds. Thus, adjacent molecules are connected through intermolecular hydrogen bonds to generate a banded structure. Furthermore, these bands are linked into an interesting 3D network via hydrogen bonds and - interactions. Fortunately, the solubilities of (8) and (9) were distinctly improved and can exceed 50 mg ml-1 in water or PBS buffer system (pH 7.4) at room temperature. In addition, the results of an investigation of anti-inflammatory activity show that (8) and (9), with o-and p-fluoro substituents, respectively, display more potential for inhibitory effects on LPS-induced NO secretion than starting ketones (6) and (7).
Sun, Yue,Gao, Zhongfei,Wang, Chunhua,Hou, Guige
p. 1157 - 1165
(2019/08/13)

Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations
Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.
Betori, Rick C.,May, Catherine M.,Scheidt, Karl A.
supporting information
p. 16490 - 16494
(2019/11/03)

Strategic Approach to the Metamorphosis of γ-Lactones to NH γ-Lactams via Reductive Cleavage and C-H Amidation
A new approach has elaborated on the conversion of γ-lactones to the corresponding NH γ-lactams that can serve as γ-lactone bioisosteres. This approach consists of reductive C-O cleavage and an Ir-catalyzed C-H amidation, offering a powerful synthetic tool for accessing a wide range of valuable NH γ-lactam building blocks starting from γ-lactones. The synthetic utility was further demonstrated by the late-stage transformation of complex bioactive molecules and the asymmetric transformation.
Jung, Hoi-Yun,Chang, Sukbok,Hong, Sungwoo
supporting information
p. 7099 - 7103
(2019/09/07)

A metal-free desulfurizing radical reductive C-C coupling of thiols and alkenes
An intermolecular reductive C-C coupling of electrophilic alkyl radicals and alkenes has been developed. Thiols were used as both hydrogen-donating reagents and alkyl radical precursors in the presence of triethyl phosphite and radical initiator. A wide range of alkenes, including styrenes, and aliphatic olefins were well tolerated in this transformation. Mechanistic studies indicated that a phosphite promoted radical desulfurization of thiols to access electrophilic alkyl radicals and a radical chain propagation process may be involved in this transformation.
Qin, Qixue,Wang, Weijing,Zhang, Cheng,Song, Song,Jiao, Ning
supporting information
p. 10583 - 10586
(2019/09/06)

Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals
In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.
Wu, Fu-Peng,Li, Da,Peng, Jin-Bao,Wu, Xiao-Feng
supporting information
p. 5699 - 5703
(2019/08/01)

An Electrophilic Trifluoromethylthiolation of Silylenol Ethers and β-Naphthols with Diethylaminosulfur Trifluoride and (Trifluoromethyl)trimethylsilane
An efficient and general trifluoromethylthiolation of silylenol ethers and β-naphthols have been accomplished employing the combination of diethylaminosulfur trifluoride (DAST) and (trifluoromethyl)trimethylsilane (CF3TMS) as source of electrophilic trifluoromethylthio moiety for the synthesis of α-trifluoromethylthiolated carbonyl compounds and β-naphthols in good yields. Important features of this method include wide functional group tolerance and use of readily available DAST/CF3TMS. Potential of the methodology was demonstrated via the synthesis of α-trifluoromethylthiolated (+)-4-cholesten-3-one and naphthoquinone. (Figure presented.).
Saravanan, Perumal,Anbarasan, Pazhamalai
supporting information
p. 2894 - 2899
(2018/08/17)

Indium-Catalyzed Direct Conversion of Lactones into Thiolactones and Selenolactones in the Presence of Elemental Sulfur and Selenium
The direct conversion of lactones into thiolactones with elemental sulfur (S 8) catalyzed by InCl 3 /PhSiH 3 in a one-pot reaction is described. This catalytic system was successfully applied to the novel preparation of selenolactones from lactones and selenium.
Sakai, Norio,Horikawa, Shuhei,Ogiwara, Yohei
p. 565 - 574
(2017/12/26)

Design, synthesis and biological evaluation of 3,4-dihydronaphthalen-1(2H)-one derivatives as Bcl-2 inhibitors
Abstract: A series of new 3,4-dihydronaphthalen-1(2H)-one derivatives (6a–f) were designed, and synthesized by the Claisen–Schmidt condensation reaction. Their structures were characterized by NMR, FTIR, and MS spectroscopy. Their antitumor activities against human neoplastic cell lines Hela, Hepg2, K562, THP-1, SW1990, MIA PaCa-2, NCI-H460 and SK-BR-3 by the MTT method exhibited obvious anticancer activities and their cytotoxicities for LO2 cell lines were lower than DOX, especially for 6b and 6d. The inhibition activities against the Bcl-2 protein for 6b was evaluated and the result shows that lipophilic 3,4-dimethoxybenzylidene and 3,4-dihydronaphthalen-1(2H)-one could bind slightly to the active pockets of the Bcl-2 protein.
Wang, Fuli,Zhang, Rongxiang,Cui, Yong,Sheng, Liping,Sun, Yinping,Tian, Wei,Liu, Xiao,Liang, Shuzeng
p. 5933 - 5942
(2017/09/23)

Substituted 4-oxo-crotonic acid derivatives as a new class of protein kinase B (PknB) inhibitors: synthesis and SAR study
Protein kinase B (PknB) is an essential serine/threonine protein kinase required for Mycobacterium tuberculosis (M. tb) cell division and cell-wall biosynthesis. A high throughput screen using PknB identified a (E)-4-oxo-crotonic acid inhibitor, named YH-8, which was used as a scaffold for SAR investigations. A significant improvement in enzyme affinity was achieved. The results indicated that the α,β-unsaturated ketone scaffold and “trans-” configuration are essential for the activity against PknB. And compounds with an aryl group, especially with electron-withdrawing substituents on benzene ring, exhibited four fold potency than that of YH-8.
Xu, Changliang,Bai, Xiaoguang,Xu, Jian,Ren, Jinfeng,Xing, Yun,Li, Ziqiang,Wang, Juxian,Shi, Jingjing,Yu, Liyan,Wang, Yucheng
p. 4763 - 4775
(2017/02/05)

Gallium-catalyzed reductive lactonization of γ-keto acids with a hydrosilane
Described herein is the GaCl3-catalyzed lactonization of γ-keto carboxylic acids in the presence of PhSiH3 leading to the direct preparation of γ-lactone derivatives. This reducing system showed a relatively wide functional group tolerance.
Sakai, Norio,Horikawa, Shuhei,Ogiwara, Yohei
p. 81763 - 81766
(2016/09/09)

Borontribromide-mediated C-C bond formation in cyclic ketones: A transition metal free approach
Borontribromide (BBr3) is a well-known demethylating agent. The current investigation was focused on a new application of borontribromide as a C-C bond forming agent in cyclic ketones. In this study, borontribromide mediated C-C bond formation reactions of tetralones, chromenone, thiochromenone and indanones were explored. A methoxy group containing ketones showed selective C-C bond formation reaction instead of demethylation of the methoxy group. MM2 steric energy calculations for the final products showed that the reaction favored the formation of exo- or endo-cyclic double bond containing products, depending upon their low MM2 steric energy in a specific frame structure, as observed in X-ray crystallography. A comprehensive crystallographic and pi-stacking analysis of product 10a demonstrated the formation of 10a as an enantiomeric mixture, and its centre of inversion was stabilized by a set of three unique pi-pi interactions.
Ahmad, Imran,Pathak, Vinay,Vasudev, Prema G.,Maurya, Hardesh K.,Gupta, Atul
p. 24619 - 24634
(2014/07/07)

Discovery of synthetic methoxy-substituted 4-phenylbutyric acid derivatives as chemical chaperones
In this study, we evaluated the chemical chaperone activity of synthetic 4-phenylbutyric acid (4-PBA) derivatives. These derivatives have a methoxy group at the benzene ring and/or longer or shorter fatty acid portions. Several 4-PBA derivatives demonstrated higher antiaggregation activity than 4-PBA. Moreover, 4-(4-methoxyphenyl)butanoic acid (7b) showed protective effects against endoplasmic reticulum stress-induced neuronal cell death.
Mimori, Seisuke,Okuma, Yasunobu,Kaneko, Masayuki,Kawada, Koichi,Nomura, Yasuyuki,Murakami, Yasuoki,Hamana, Hiroshi
supporting information
p. 1051 - 1052
(2013/09/24)

PROCESS FOR THE PREPARATION OF N-[2- (7-METHOXY-L-NAPHTHYL) ETHYL] ACETAMIDE AND ITS NOVEL CRYSTALLINE FORMS
The present invention relates to a process for the preparation of N-[2-(7-methoxy-l-naphthyl)ethyl]acetamide compound of formula-1 and novel crystalline forms of its intermediates as well as the final compound.
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(2012/04/23)

Carboxylation of alkylboranes by N-heterocyclic carbene copper catalysts: Synthesis of carboxylic acids from terminal alkenes and carbon dioxide
Caught in the act: N-Heterocyclic carbene copper(I) complexes (1; IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) serve as an excellent catalyst for the carboxylation of alkylboranes (2; R=alkyl) with CO2 to afford a variety of functionalized carboxylic acids (3) in high yields. A novel copper methoxide/alkylborane adduct (A) and its subsequent CO2 insertion product (B) have been isolated and shown to be true active catalyst species.
Ohishi, Takeshi,Zhang, Liang,Nishiura, Masayoshi,Hou, Zhaomin
supporting information; experimental part
p. 8114 - 8117
(2011/10/18)

Peptide/laccase cocatalyzed asymmetric α-oxyamination of aldehydes
An asymmetric α-oxyamination could be successfully performed by a peptide catalyst and laccase. The combination of peptide catalysis and enzymatic air oxidation promoted the reaction smoothly in water without employing a metal reagent. The oxyaminated compounds could be obtained as both aldehyde and carboxylic acid products depending on the reaction conditions.
Akagawa, Kengo,Kudo, Kazuaki
scheme or table
p. 3498 - 3501
(2011/09/14)

Facile and efficient hydrolysis of organic halides, epoxides, and esters with water catalyzed by ferric sulfate in a PEG1000-DAIL[BF 4]/toluene temperature-dependent biphasic system
An efficient and environmentally friendly procedure for the hydrolysis of organic halides, epoxides, and esters with water catalyzed by ferric sulfate in a PEG1000-DAIL[BF4]/toluene temperature-dependent biphasic system has been developed. The product can be easily isolated by a simple decantation, and the catalytic system can be recycled and reused without loss of catalytic activity.
Hu, Yu Lin,Jiang, Hui,Zhu, Jie,Lu, Ming
experimental part
p. 292 - 298
(2011/04/21)

PHENYLALKYLCARBOXYLIC ACID DELIVERY AGENTS
The present invention provides phenylalkylcarboxylic acid compounds and compositions containing such compounds which facilitate the delivery of biologically active agents.
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(2008/12/07)

Discovery of a highly orally bioavailable c-5-[6-(4-Methanesulfonyloxyphenyl)hexyl]-2-methyl-1,3-dioxane-r-2-carbo xylic acid as a potent hypoglycemic and hypolipidemic agent
A series of novel 1,3-dioxane-2-carboxylic acid derivatives containing alkyl chain tether and substituted phenyl group as a lipophilic tail have been prepared as agonists of PPARα and γ. c-5-[6-(4-Methanesulfonyloxyphenyl)hexyl]-2-methyl-1,3-dioxane-r-2-carbo xylic acid 13c exhibited potent hypoglycemic and lipid lowering activity with high oral bioavailability in animal models.
Pingali, Harikishore,Jain, Mukul,Shah, Shailesh,Basu, Sujay,Makadia, Pankaj,Goswami, Amitgiri,Zaware, Pandurang,Patil, Pravin,Godha, Atul,Giri, Suresh,Goel, Ashish,Patel, Megha,Patel, Harilal,Patel, Pankaj
scheme or table
p. 5586 - 5590
(2009/06/18)

Asymmetric hydrogenation of α-primary and secondary amino ketones: Efficient asymmetric syntheses of (-)-arbutamine and (-)-denopamine
Two ss-receptor agonists (-)-denopamine and (-)-arbutamine were prepared in good yields and enantioselectivities by asymmetric hydrogenation of unprotected amino ketones for the first time by using Rh catalysts bearing electron-donating phosphine ligands. A series of α-primary and secondary amino ketones were synthesized and hydrogenated to produce various 1,2-amino alcohols in good yields and with good enantioselectivies. This Rh electron-donating phosphine-catalyzed asymmetric hyderogenation repI resents one of the most promising and convenient approaches towards the asymmetric synthesis of chiral amino alcohols.
Shang, Gao,Liu, Duan,Allen, Scott E.,Yang, Qin,Zhang, Xumu
p. 7780 - 7784
(2008/04/03)

BENZOTHIAZIN-3-ONE COMPOUND AND INTERMEDIATE THEREFOR
A medicine which contains as an active ingredient a benzothiazin-3-one-compound represented by the formula (1): (wherein n is 3 or 4; R represents ethyl or hydrogen; and R 1 represents hologeno, alkoxy, haloalkyl, or haloalkoxy) or a pharmaceutically acceptable salt thereof. It is useful as a therapeutic or preventive agent for arthrosis deformans, chondrodegenerative discases such as chronic articular rheumatism, cancers, gingivitis, etc. Also provided are an intermediate for the compound and a process for producing the compound.
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(2008/06/13)

A facile synthesis of di-O-methyl centrolobol
A facile route to (±)di-O-methyl centrolobol 4 has been explored starting from 4-oxo-4-(4-methoxyphenyl) butanoic acid 7 and 4-methoxycinnamic acid 13.
Panda, Atulya Kumar
p. 372 - 375
(2007/10/03)

Synthesis of Methoxy-2-hydroxy-1,4-naphthoquinones and Reaction of One Isomer with Aldehydes under Basic Conditions
Two protocols for the synthesis of methoxy-2-hydroxy-1,4-naphthoquinones were investigated in order to evaluate their behavior towards aldehydes under amine-basic conditions. Both the nature of the quinone and aliphatic aldehyde contribute to the viability of this condensation as well as further transformations.
Ameer, Farouk,Giles, Robin G. F.,Green, Ivan R.,Pearce, Rene
p. 1247 - 1258
(2007/10/03)

Synthesis of 1-tetralone derivatives using a Stille cross coupling/friedel crafts acylation sequence
An efficient method of synthesis of 1-tetralones has been achieved featuring a Stille cross-coupling reaction as the key step.
Vercouillie, Johnny,Abarbri, Mohamed,Parrain, Jean-Luc,Duchene, Alain,Thibonnet, Jerome
p. 3751 - 3762
(2007/10/03)

A convenient procedure for parallel ester hydrolysis
The treatment of alkyl esters with barium hydroxide octahydrate in methanol followed by protonation with anhydrous hydrogen chloride affords carboxylic acids. The procedure does not require aqueous workup and is particularly suitable for parallel synthesis applications.
Anderson, Marc O.,Moser, Jamie,Sherrill, John,Guy, R. Kiplin
p. 2391 - 2393
(2007/10/03)

Synthesis and antitumor activity of tanshinone analogues
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Aisa, Haji Akber,Lu, Wei,Cai, Junchao
p. 404 - 406
(2007/10/03)

Titanium-mediated carboxylation of alkynes with carbon dioxide
The regioselective carboxylation of nonactivated internal alkynes can be performed with carbon dioxide under atmospheric pressure using a simple procedure based on the chemistry of Sato-type diisopropyloxytitanacyclopropenes. Various polysubstituted vinylcarboxylic acids and butenolides can be prepared in this way. In addition, this paper describes an experimental protocol for the preparation of solutions of (η2-cyclopentene)diisopropyloxytitanium. This complex also reacts with carbon dioxide, and mediates pinacol coupling of acetophenone. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Six, Yvan
p. 1157 - 1171
(2007/10/03)

The Huang-Minlon modification of Wolff-Kishner reduction in rapid and simple way using microwave technology
A high yielding, simple and fast method for the reduction of various aldehydes and ketones to the respective hydrocarbons following Huang-Minlon modification tender microwave irradiation is described.
Chattopadhyay, Sarmishtha,Banerjee, Sajal Kumar,Mitra, Alok Kumar
p. 906 - 907
(2007/10/03)

Direct synthesis of γ-butyrolactones via γ-phenyl substituted butyric acids mediated benzyl radical cyclization
Synthesis of several γ-butyrolactones with aromatic substitution at carbon 5 from comparative γ-aryl acids with 25-85% yield are covered. The straight oxidation in the presence of peroxydisulphate-copper(II)chloride system in aqueous medium was applied. The reaction is highly regioselective and leads exclusively to γ-butyrolactone, through stable benzylic radical intermediate.
Mahmoodi,Jazayri
p. 1467 - 1475
(2007/10/03)

Synthesis of an intermediate, 7,8-dimethyl-2-tetralone, for occidol isomer-I and occidol isomer-II
Anisole is succinoylated with succinic anhydride to yield 3-(p-methoxybenzoyl) propionic acid 3.The acid on Clemmensen reduction gives 4-(p-methoxy phenyl) butyric acid 4 which on esterification affords methyl 4-(p-methoxy-phenyl)butyrate 5.The ester 5 on reaction with methyl-magnesium iodide gives 5-(p-methoxyphenyl)-2-methyl-pentan-2-ol 6 which is cyclised with PPA to furnish 7-methoxy-1,1-dimethyltetralin 7.The tetralin 7 undergoes aromatization with p-chloranil or DDQ to afford 7-methoxy-1,2-dimethyl naphthalene 8, tike reduction of which with sodium in liquid ammonia as welt as with sodium in ethanol yields 7,8-dimethyl-2-tetralone 10.
Bachule, M. T.,Mane, R. B.
p. 281 - 284
(2007/10/03)

Transition-Metal-Catalyzed Oxidations, 11.1 Total Synthesis of (±)-Lacinilene C Methyl Ether by β-Naphthol to α-Ketol Oxidation
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Krohn, Karsten,Zimmermann, Gregor
p. 4140 - 4142
(2007/10/03)

Use of a dipeptide chemical library in the development of non-peptide tachykinin NK3 receptor selective antagonists
The use of a dipeptide library as the source of a micromolar chemical lead compound for the human tachykinin NK3 receptor is described. The screening of a dipeptide library through a cloned human NK3 receptor binding assay resulted in the identification of Boc(S)Phe(S)PheNH2 (1), which has subsequently been developed, following a 'peptoid' design strategy, into a series of high-affinity NK3 receptor selective antagonists. The structure- activity relationship of the C-terminal portion of this dipeptide lead was first explored and led to the identification of the urea derivative Boc(S)Phe(R)αMePheNH(CH2)7NHCONH2 (41, PD157672). This modified dipeptide has a K(o) of 7 nM in blocking senktide-induced increases in intracellular calcium levels in human NK3 receptors stably expressed in CHO cells. Subsequent optimization of the N-terminal BocPhe group and the αMePhe residue side chain of 41 led to the identification of [S-(R*,S*)]-[2-(2,3- difluorophenyl)-1-methyl-1-[(7-ureidoheptyl)carbamoyl]ethyl]carbamic acid 2- methyl-1-phenylpropyl ester (60, PD161182), a non-peptide NK3 receptor selective antagonist. Compound 60 blocks the senktide-evoked increases in intracellular calcium levels in cloned human NK3 receptors stably expressed in CHO cells with K(e) of 0.9 nM.
Boden, Phil,Eden, Jon M.,Hodgson, Julie,Horwell, David C.,Hughes, John,McKnight, Alexander T.,Lewthwaite, Russell A.,Pritchard, Martyn C.,Raphy, Jenny,Meecham, Ken,Ratcliffe, Giles S.,Suman-Chauhan, Nirmala,Woodruff, Geoffrey N.
p. 1664 - 1675
(2007/10/03)

Structure Elucidation and Total Synthesis of New Tanshinones Isolated from Salvia miltiorrhiza Bunge (Danshen)
Totally 11 new compounds have been isolated from the dried root of Salvia miltiorrhiza Bunge "Danshen" and their structures were elucidated by means of spectrometric methods.The total syntheses of two new compounds, namely, 1,2-didehydromiltirone and 4-methylenemiltirone, are also reported.
Chang, Hson Mou,Cheng, Kwok Ping,Choang, Tai Francis,Chow, Hak Fun,Chui, Kuk Ying,et al.
p. 3537 - 3543
(2007/10/02)

An approach to the biomimetic synthesis of aryltetralin lignans
The BF3 catalysed cyclisation of 3-arylpropyl substituted quinone-methide ketals affords a mild, biomimetic route to aryltetralins. 1H- and 13C-NMR spectra of the products are reported.
Pelter, Andrew,Ward, Robert S.,Rao, Ramohan R.
p. 2933 - 2938
(2007/10/02)

Methods for the Construction of Linear 1,7-Diarylheptanoids; Synthesis of Di-O-methylcentrolobol and Precursors (Synthetic and Biosynthetic) to the meta,meta-Bridged Biphenyls Myricanol and Myricanone
1,7-diarylheptanoids are a varied natural product class in which 'linear' types appear to be biosynthetic precursors to macro(carbo)cyclic (3), macro(oxa)cyclic (4), and condensed polycyclic (5) examples.Various methods (suitable for radiolabelling) are described for constructing 'linear' diarylheptanoids, including Grignard couplings (employing activated magnesium) with arylpropanals and oxazonium salts (11a), (11h), (15a), and (15b)> and dithian alkylation (15c)>.Alkyl-lithium treatment of the benzyloxydithian (19b) gave 1,2,3-triphenylcyclopropane.Syntheses via trialkylcyanoborates were frustrated by disproportionation of the intermediate trialkylboranes.The diarylheptanoids synthesised (11a-h) and (15a-e) include synthetic and biosynthetic precursors to meta,meta-bridged biphenyls and related macrocyclic ethers.
Henley-Smith, Peter,Whiting, Donald A.,Wood, Andrew F.
p. 614 - 622
(2007/10/02)