cas 2999-40-8, PHLOROGLUCINOL TRIACETATE | Articles data

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COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USE THEREOF AS INHIBITORS OF RAN GTPASE
Compounds of general formula IA, IB and IC outlined below, including pharmaceutically acceptable salts, solvates and hydrates thereof. Such compounds and pharmaceutical compositions comprising them may be used in medical conditions involving Ran GTPase.
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Paragraph 0097; 00120

(2019/04/09)

Protection of COOH and OH groups in acid, base and salt free reactions
We report an iron-catalyzed general functional group protection method with inexpensive reagents. This environmentally benign process does not use acids or bases, and does not produce waste products. Further purification beyond filtration and evaporation is, in most cases, unnecessary. Free COOH and OH groups can be protected in a one-pot reaction.
Zhu, Xiaotao,Qian, Bo,Wei, Rongbiao,Huang, Jian-Dong,Bao, Hongli
supporting information
p. 1444 - 1447
(2018/04/12)

Benzofuro[3,2-d]pyrimidines inspired from cercosporamide CaPkc1 inhibitor: Synthesis and evaluation of fluconazole susceptibility restoration
In a context of growing resistance to classical antifungal therapy, the design of new drugs targeting alternative pathways is highly expected. Benzofuro[3,2-d]pyrimidine derivatives, derived from (?)-cercosporamide, were synthesized and evaluated as potential Candida albicans PKC inhibitors in the aim of restoring susceptibility to azole treatment. Co-administration assay of benzofuropyrimidinedione 23 and fluconazole highlighted a synergistic effect on inhibition of cell growth of a Candida albicans resistant strain.
Dao, Viet Hung,Ourliac-Garnier, Isabelle,Bazin, Marc-Antoine,Jacquot, Catherine,Baratte, Blandine,Ruchaud, Sandrine,Bach, Stéphane,Grovel, Olivier,Le Pape, Patrice,Marchand, Pascal
p. 2250 - 2255
(2018/05/30)

The synthesis of lactone-bridged 1,3,5-triphenylbenzene derivatives as pi-expanded coumarin triskelions
Two triply lactone-bridged 1,3,5-triphenylbenzene derivatives with solubilizing moieties have been synthesized in five and six steps from commercially available starting materials. Compounds containing the 1,3,5-triphenylbenzene core with two atom bridges are relatively unknown. This new class of pi-expanded coumarins contain triskelion architectures and X-ray crystallographic studies of one of the triskelions indicates that the 1,3,5-triphenylbenzene core adopts a near-planar geometry. This is the only known example of a two atom-bridged 1,3,5-triphenylbenzene derivative to adopt a planar structure.
Hintz, Heather A.,Sortedahl, Nicholas J.,Meyer, Samantha M.,Decato, Daniel A.,Dahl, Bart J.
supporting information
p. 4703 - 4708
(2017/11/17)

Synthesis and antibacterial activity of new symmetric polyoxygenated dibenzofurans
A series of symmetric polyoxygenated dibenzofurans with 2-methylbutyril moieties at C-4 and C-6 were obtained from commercial phloroglucinol through a sequence of reactions that include monoacylation, iodination, Suzuki-Miyaura coupling, oxidative dimeriz
Oramas-Royo, Sandra,Pantoja, Kriss Dayana,Amesty, ángel,Romero, Carmen,Lorenzo-Castrillejo, Isabel,Machín, Félix,Estévez-Braun, Ana
p. 178 - 187
(2017/10/16)

Microwave-assisted acetylation of phenols without catalyst under solvent free condition
Etherification between phenols with acetic anhydride was tested under different conditions. Phenols were efficiently acylated with acetic anhydride to give phenol acetate derivatives in good high yields without catalyst and solventless conditions under microwave irradiation.
Zhang, Yu-Quan,Li, Yan-Chun,Zhu, Ji-Hua,Li, Zhi-Feng,Guo, Guo-Zhe,Chen, Dong-Ping
p. 7746 - 7748
(2015/02/02)

Synthesis and antiproliferative activity of benzofuran-based analogs of cercosporamide against non-small cell lung cancer cell lines
A novel series of 3-methyl-1-benzofuran derivatives were synthesized and screened in vitro for their antiproliferative activity against two human NSCLC cell lines (NSCLC-N6 mutant p53 and A549 wild type p53). Most promising compounds presented a structural analogy with the west part of cercosporamide, a natural product of biological interest. In particular, compounds 10, 12 and 31 showed cytotoxic activities at micromolar concentrations (IC50 50 values (25-40 μM).
Bazin, Marc-Antoine,Bodero, Lizeth,Tomasoni, Christophe,Rousseau, Bénédicte,Roussakis, Christos,Marchand, Pascal
p. 823 - 832
(2013/10/22)

SYNTHESIS OF CATECHIN AND EPICATECHIN CONJUGATES
The present invention relates generally to catechin and epicatechin conjugates of formula (I). For example, a chemical synthesis process for the preparation of catechin and epi-catechin compounds, in particular of catechin and epi-catechin conjugates is disclosed. A further aspect of the invention pertains to new catechin and epi-catechin conjugate compounds.
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Page/Page column 13-14

(2013/03/26)

Synthesis of catechin and epicatechin conjugates
The present invention relates generally to catechin and epicatechin conjugates of formula (I). For example, a chemical synthesis process for the preparation of catechin and epi-catechin compounds, in particular of catechin and epi-catechin conjugates is disclosed. A further aspect of the invention pertains to new catechin and epi-catechin conjugate compounds.
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Paragraph 0038

(2013/03/26)

O-acetylation: Synthesis of acetylated phenols from aryl-methyl ethers over boron alkoxides
A new acetylation procedure has been applied to 13 aryl-methyl ethers using boron chemistry. In this procedure, demethylation of aryl-methyl ethers and acetylation of the resulting phenols were combined into one procedure in order to shorten the number of stages and to achieve easy purification. Eleven known with/without bromine and two new [bis(3,4-diacetoxyphenyl)methanone and 5,5'-methylenebis(1,2-diacetoxy-3,4-dibromobenzene) (a natural bromophenol's acetylated derivative)] acetylated arene compounds were synthesised from their methoxy derivatives by this method. The effectiveness of the method was illustrated by producing an acetylated natural bromophenol from its methyl ether. The phenol form was obtained by hydrolysing the acetylated natural bromophenol. Thus, the advantage of this method in the natural product chemistry of phenolic compounds was confirmed.
Balaydin, Halis T.
scheme or table
p. 238 - 240
(2012/09/08)

Synthesis and evaluation of benzophenone O-glycosides as α-glucosidase inhibitors
The first total synthesis of benzophenone O-glycosides (iriflophenone 2-O-α-L-rhamnopyranoside: 1 and aquilarisinin: 2) isolated from the leaves of Aquilaria sinensis and related new derivatives (3-12) was accomplished through suitable protecting group ma
Liu, Qingchao,Guo, Tiantian,Li, Wenhong,Li, Dong,Feng, Zili
p. 771 - 783
(2013/01/15)

Highly efficient solvent-free acetylation of alcohols with acetic anhydride catalyzed by recyclable sulfonic acid catalyst (SBA-15-Ph-Pr-SO3H)- An environmentally benign method
The catalytic activity of highly thermal stable, hydrophobic, and complete heterogeneous propylsulfonic acid functionalized nanostructured SBA-15 for excellent acetylation of alcohols and phenols with acetic anhydride at ambient temperature in solvent-free conditions was examined under environmentally benign reaction conditions. The salient features of this protocol are the absence of solvent, a green experimental procedure, and simple reusability of the catalyst (at least five reaction cycles).
Zareyee, Daryoush,Ghadikolaee, Abdollah Razaghi,Khalilzadeh, Mohammad A.
experimental part
p. 464 - 468
(2012/06/16)

One pot synthesis and anticancer activity of dimeric phloroglucinols
A series of dimeric phloroglucinol compounds were synthesized in a single step using commercially available phloroglucinol and methanesulfonic acid. Based on the reported anticancer activity of plant derived dimeric phloroglucinols, these synthesized comp
Chauthe, Siddheshwar K.,Bharate, Sandip B.,Periyasamy, Giridharan,Khanna, Amit,Bhutani, Kamlesh K.,Mishra, Prabhu D.,Singh, Inder P.
scheme or table
p. 2251 - 2256
(2012/05/04)

Novel double-SO3h functionalized ionic liquid for acetylation
Novel double-SO3H functionalized ionic liquid (DFIL) was synthesized and its catalytic activities for acetylation studied. The result showed that the DFIL possess high acidity and was very efficient for the acetylation of alcohols, amines and phenols with good to excellent yields in short reaction times. Operational simplicity, stability to water and air, small amounts needed, low cost, high yields, high acidity, applicability to large-scale reactions and reusability are the key features of the DFIL, which indicated promising applications of DFIL in green chemical processes. Pleiades Publishing, Ltd., 2012.
Zhu, Lili,Liang, Xuezheng
p. 684 - 688
(2013/02/23)

Broensted acidic ionic liquid as an efficient catalyst for acetylation of alcohols and phenols
A novel Broensted acidic room temperature ionic liquid (1-H-3-methyl-imidazolium bisulfate) is found to catalyze efficiently the acetylation of a wide rang of alcohols as well as phenols with acetic anhydride in good to excellent yields at 50°C under solvent-free conditions. Products are easily isolated by extraction with ether and the protocol is mild and green, compared to the existing method based on toxic solvents.
Hajipour, Abdol R.,Khazdooz, Leila,Ruoho, Arnold E.
experimental part
p. 398 - 403
(2009/12/06)

C-Glucosylflavonoid biosynthesis from 2-hydroxynaringenin by Desmodium uncinatum (Jacq.) (Fabaceae)
[2′,3′,5′,6′-2H4]-2-Hydroxynaringenin is synthesised and incubated with commercially available UDP-glucose and the crude protein extract from Desmoduim uncinatum leaves. The organic extract produces isotopically labelled [2′,3′,5′,6′-2H4]-vitexin and [2′,3′,5′,6′-2H4]-isovitexin. Repeating the experiment with denatured protein or replacing the 2-hydroxynaringenin with [2′,3′,5′,6′-2H4]-apigenin or [2′,3′,5′,6′-2H4]-naringenin results in no observable incorporation. 2-Hydroxynaringenin is therefore the substrate for C-glucosylflavonoid biosynthesis in D. uncinatum.
Hamilton, Mary L.,Caulfield, John C.,Pickett, John A.,Hooper, Antony M.
scheme or table
p. 5656 - 5659
(2011/02/24)

Molecular iodine in isopropenyl acetate (IPA): a highly efficient catalyst for the acetylation of alcohols, amines and phenols under solvent free conditions
Iodine in isopropenyl acetate (IPA) is a highly efficient catalyst for the acetylation of a variety of alcohols, phenols and amines under solvent free conditions. Primary, secondary, tertiary alcohols, amines and mono to polyhydroxy phenols and anilines with electron donating or withdrawing substituents can be easily acetylated in good to excellent yield at 85-90 °C.
Ahmed, Naseem,van Lier, Johan E.
p. 5345 - 5349
(2007/10/03)

Dodecamethoxy- and hexaoxotricyclobutabenzene: Synthesis and characterization
We report herein the syntheses of dodecamethoxytricyclobutabenzene (TCBB) 1 and hexaoxo-TCBB 2, a class of molecules with structural and theoretical interest. The preparation is based on the 3-fold [2 + 2] cycloadditions of benzyne and ketene silyl acetal
Hamura, Toshiyuki,Ibusuki, Yousuke,Uekusa, Hidehiro,Matsumoto, Takashi,Siegel, Jay S.,Baldridge, Kim K.,Suzuki, Keisuke
p. 10032 - 10033
(2007/10/03)

Aerobic oxidation of 1,3,5-triisopropylbenzene using N-hydroxyphthalimide (NHPI) as key catalyst
The first systematic study on the aerobic oxidation of 1,3,5- triisopropylbenzene was examined by the use of N-hydroxyphthalimide (NHPI) as a key catalyst. It was found that 1,3,5-triisopropylbenzene was efficiently oxidized with O2 in the presence of a catalytic amount of NHPI and azobisisobutyronitrile (AIBN) at 75°C. Upon treatment of the resulting products with sulfuric acid followed by acetic anhydride led to 5-acetoxy-1,3-diisopropylbenzene and 3,5-diacetoxy-1-isopropylbenzene as major products and a small amount of 1,3,5-triacetoxybenzene. When t-butylperoxypivalate (BPP) was employed as a radical initiator, the oxidation could be achieved in good yield even at 50°C. This oxidation provides a facile method for preparing phenol derivatives bearing an isopropyl moiety, which can be used as pharmaceutical starting materials.
Aoki, Yasuhiro,Hirai, Naruhisa,Sakaguchi, Satoshi,Ishii, Yasutaka
p. 10995 - 10999
(2007/10/03)

Rapid formation of acetates under microwave irradiation using montmorillonite acid clay catalyst
The combination of microwave irradiation and montmorillonite [H +] clay catalyst dramatically enhances the rate of formation of acetates of alcohols, phenols and amines when treated with acetic anhydride. A series of acetates have been prepared with significantly low reaction times in very good to excellent yields.
Mallavadhani, Uppuluri V.,Sahoo, Laxmidhar,Roy, Subhra
p. 2175 - 2177
(2007/10/03)

A rapid and efficient method for acetylation of phenols with acetic anhydride catalysed by TiO2/SO42- solid superacid
A rapid and efficient method for acetylation of phenols with acetic anhydride in the presence of TiO2/SO42- solid superacid at room or at reflux temperature in excellent yield is described.
Ma, Yan-Ran,Jin, Tong-Shou,Wang, Zhen-Hua,Li, Tong-Shuang
p. 1777 - 1778
(2007/10/03)

An efficient and simple procedure for acetylation of alcohols and phenols with acetic anhydride catalysed by expansive graphite
Acetylation of alcohols and phenols with acetic anhydride has been carried out in excellent yield under catalysis of expansive graphite.
Jin, Tong-Shou,Ma, Yan-Ran,Li, Tong-Shuang,Zhang, Zhan-Hui,Duan, Guang-Bo
p. 109 - 110
(2007/10/03)

Crystal and molecular structure of 1,3,5-trimethoxy-2,4,6-trinitrobenzene. Mesomeric effects for out-of-plane twisted substituents
Crystal and molecular structure of 1,3,5-trimethoxy-2,4,6-trinitrobenzene has been determined by X-ray diffraction technique. Crystal data for C9H9N3O9: triclinic, P1, a = 7.507(2) A, b = 9.218(2) A, c = 10.426(
Anulewicz-Ostrowska,Krygowski,Cyranski,Matuszewska
p. 1895 - 1901
(2007/10/03)

Synthesis of a non-peptide analogue of omega-conotoxin MVIIA
An efficient synthesis of an alkylphenyl ether based peptidomimetic is described. The compound mimics three key amino acids of omega-conotoxin MVIIA from the cone shell Conus magus and may provide an entry to the design of low molecular weight antagonists of N-type neuronal calcium channels.
Menzler, Stefan,Bikker, Jack A.,Horwell, David C.
p. 7619 - 7622
(2007/10/03)

Sulfamic acid catalysed acetylation of alcohols and phenols with acetic anhydride
An easy acetylation of alcohols and phenols with acetic anhydride has been carried out in excellent yield under catalysis of sulfamic acid.
Jin, Tong-Shou,Ma, Van-Ran,Zhang, Zhan-Hui,Li, Tong-Shuang
p. 3173 - 3177
(2007/10/03)

Montmorillonite clay catalysis. Part 10. K-10 and KSF-catalysed acylation of alcohols, phenols, thiols and amines: Scope and limitation
Montmorillonite K-10 and KSF are highly efficient catalysts for the acetylation of a variety of alcohols, thiols, phenols and amines with acetic anhydride. Amino groups can be selectively acetylated in the presence of hydroxy groups, while the hydroxy groups can be preferentially acetylated in the presence of thiol groups. No selectivity is observed between primary and secondary hydroxy groups in the presence of K-10 and KSF. The catalysts are found not to be efficient for acetylation of tertiary alcohols. This method is simple and convenient with minimum environmental impact. The catalysts are also effective for the acylation of alcohols, thiols, phenols and amines with acetyl chloride and benzoyl chloride. Cyclic anhydrides such as succinic anhydride, maleic anhydride and phthalic anhydride and p-toluene sulfonyl chloride show less reactivity than acetic anhydride and acyl chlorides.
Li, Tong-Shuang,Li, Ai-Xiao
p. 1913 - 1917
(2007/10/03)

Montmorillonite K-10 and KSF as remarkable acetylation catalysts
Montmorillonite K-10 and KSF catalyse the acetylation of alcohols, thiols, phenols and amines with acetic anhydride in excellent yield.
Li, Ai-Xiao,Li, Tong-Shuang,Ding, Tian-Hui
p. 1389 - 1390
(2007/10/03)

All-cis-1,3,5-triamino-2,4,6,-cyclohexanetriol derivatives, their use, processes for their preparation and pharmaceutical preparations containing them
All-cis-1,3,5-Triamino-2,4,6-trihydroxycyclohexane derivatives corresponding to the general formula I STR1 wherein the symbols R1, R2, R3, R4, R5 and R6 are identical or different and represent hydrogen atoms, alkyl groups or --CO-alkyl groups wherein the alkyl in the alkyl or --CO-alkyl group has 1 to 18 carbon atoms and the alkyl and --CO-alkyl groups may contain, independently of one another, one or more identical or different functional groups, and at least one of the groups R1 to R6 is one of the above mentioned unsubstituted or substituted alkyl groups or --CO-alkyl groups, and their salts with pharmacologically conventionally used inorganic or organic acids and their quaternary ammonium salts, processes for their preparation and their use, and pharmaceutical preparations containing these compounds.
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(2008/06/13)

BIOSYNTHESIS OF THE 3-ETHYLCHROMONE PHYTOALEXIN LATHODORATIN IN LATHYRUS ODORATUS
Feeding experiments with 14C- and 13C-labelled precursors have demonstrated that the phloroglucinol ring of the 3-ethylchromone phytoalexin lathodoratin from cupric sulphate-induced pods of sweet pea (Lathyrus odoratus) has a polyketide origin.The remaini
Al-Douri, Nidhal A.,Dewick, Paul M.
p. 775 - 784
(2007/10/02)

A New Method for the Degradation of Anthocyanidins, Flavones, Chalcones, and Coumarins
After transformation into the corresponding chalcone or flavenol acetates anthocyanidins are oxidatively cleaved with ruthenium tetroxide to yield benzoic acid derivatives of the rings A and B.Flavones, chalcones, and coumarins are degradated by the same method.
Mentlein, Rolf,Vowinkel, Erich,Wolf, Bernd
p. 401 - 406
(2007/10/02)