- Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)
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N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.
- Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh
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supporting information
(2021/01/04)
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- Preparation method of 3-methoxy-4-hydroxybenzaldehyde
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The invention discloses a preparation method of 3-methoxy-4-hydroxybenzaldehyde, which belongs to the technical field of biochemical technology materials. The method comprises the following specific steps of adding o-chlorophenol, anhydrous aluminum chloride and toluene into a three-neck flask, stirring for dissolving, heating for reflux, then adding diethylamine, continuously refluxing, adding formic anhydride lithium salt, adjusting the PH value, carrying out suction filtration, carrying out reduced pressure distillation, and collecting fractions to obtain 3-chloro-4-hydroxybenzaldehyde, and adding the obtained 3-chloro-4-hydroxybenzaldehyde, anhydrous magnesium chloride and benzene into a three-neck flask, mixing, dissolving, heating, refluxing, dropwise adding a 10% sodium hydroxide solution, uniformly adding sodium methoxide in three batches, cooling to room temperature, adjusting the PH value, carrying out suction filtration, and carrying out reduced pressure distillation to finally obtain the 3-methoxy-4-hydroxybenzaldehyde product. Compared with a traditional method, the synthetic route is not long, the reaction condition is mild, and the yield is high.
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Paragraph 0029-0030; 0034-0035; 0039-0040; 0044-0045
(2021/08/06)
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- Towards the total synthesis of chondrochloren A: Synthesis of the (Z)-enamide fragment
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The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was o
- Geldsetzer, Jan,Kalesse, Markus
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supporting information
p. 670 - 673
(2020/05/14)
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- PRODRUGS OF FUSED-BICYCLIC C5aR ANTAGONISTS
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The present disclosure provides, inter alia, Compounds of Formulae IA, IB, IC, IIA, IIB and IIC or pharmaceutically acceptable salts thereof that are modulators of the C5a receptor. Also provided are pharmaceutical compositions and methods of use including the treatment of diseases or disorders involving pathologic activation from C5a and non-pharmaceutical applications.
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Paragraph 0249
(2019/10/23)
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- Rate enhancements due to ultrasound in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic compounds in presence of KHSO4/KCl
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Chlorination of aromatic compounds underwent magnificent rate accelerations in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic hydrocarbons in the presence of KCl and KHSO4. Reaction times reduced highly significantly from 4-5 h in conventional protocol to 30-40 min under sonication, followed by high yields of monochloro derivatives as products with high regioselectivity.
- Rajanna,Rao, A. Sambashiva,Chakravarthi,Reddy, K. Rajendar
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p. 167 - 170
(2017/12/26)
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- A process for preparing a broad pH fluorescent probe of the organic compound and use thereof (by machine translation)
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The present invention discloses a process for the preparation of a wide range of fluorescent probe in the pH of the organic compound, the organic compound can be produced according to the actual need to carry out any proportion of combination, and can be fixed in the hydrophilic high polymer further preparing and detecting water environment acidity and alkalinity of the product. The product can be realized to the pH value of the continuous measuring, thereby greatly improving the efficiency, sensitivity and repeatability. (by machine translation)
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Paragraph 0138; 0139
(2018/04/03)
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- Fluorescent pH-Responsive Probes Based on Water-Soluble Boron-Dipyrromethene (BODIPY) Derivatives, Featuring Long-Wavelength Emission
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We describe here the synthesis of water-soluble red/NIR-emissive, boron-dipyrromethene (BODIPY) derivatives displaying optical (absorption and emission) responses in pH range of 4–8. Substitution close to the tertiary aniline or the phenol subunits select
- Sutter, Alexandra,Elhabiri, Mourad,Ulrich, Gilles
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p. 11119 - 11130
(2018/08/09)
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- Regioselective C-H chlorination: Towards the sequential difunctionalization of phenol derivatives and late-stage chlorination of bioactive compounds
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We have developed a protocol for the auxillary directed C-H chlorination of phenol derivatives using catalytic amounts of palladium acetate that is amenable to the late-stage chlorination of diflufenican and estrone. The 2-pyridine group allows for a highly efficient palladium-catalyzed chlorination and sequential ortho C-H functionalization reaction of phenol derivatives to produce a variety of symmetrical and unsymmetrical 2,4,6-trisubstituted phenols.
- Gao, Chao,Li, Hongchen,Liu, Miaochang,Ding, Jinchang,Huang, Xiaobo,Wu, Huayue,Gao, Wenxia,Wu, Ge
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p. 46636 - 46643
(2017/10/16)
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- Exploration of phenylpropanoic acids as agonists of the free fatty acid receptor 4 (FFA4): Identification of an orally efficacious FFA4 agonist
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The long chain free fatty acid receptor 4 (FFA4/GPR120) has recently been recognized as lipid sensor playing important roles in nutrient sensing and inflammation and thus holds potential as a therapeutic target for type 2 diabetes and metabolic syndrome. To explore the effects of stimulating this receptor in animal models of metabolic disease, we initiated work to identify agonists with appropriate pharmacokinetic properties to support progression into in vivo studies. Extensive SAR studies of a series of phenylpropanoic acids led to the identification of compound 29, a FFA4 agonist which lowers plasma glucose in two preclinical models of type 2 diabetes.
- Sparks, Steven M.,Aquino, Christopher,Banker, Pierette,Collins, Jon L.,Cowan, David,Diaz, Caroline,Dock, Steven T.,Hertzog, Donald L.,Liang, Xi,Swiger, Erin D.,Yuen, Josephine,Chen, Grace,Jayawickreme, Channa,Moncol, David,Nystrom, Christopher,Rash, Vincent,Rimele, Thomas,Roller, Shane,Ross, Sean
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p. 1278 - 1283
(2017/06/19)
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- Synthesis of salicylaldehydes from phenols via copper-mediated duff reaction
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A copper-mediated Duff reaction for ortho-selective formylation of phenols has been developed. In the presence of copper species, significant improvements of yield and ortho-selectivity of the Duff formylation were achieved, which provides an easy access to salicylaldehydes from phenols.
- Fu, Xue-Wen,Pu, Wen-Chen,Zhang, Guo-Lin,Wang, Chun
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p. 8147 - 8158
(2015/02/19)
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- A highly efficient approach to vanillin starting from 4-cresol
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A highly efficient approach to the famous flavor and fragrance compound vanillin has been developed starting from 4-cresol with the attention focused on improving the sustainability of all the reactions. The approach involves a three-step sequence of the quasi-quantitative selective clean oxybromination of 4-cresol, the high-yield selective aerobic oxidation of 2-bromo-4-cresol, and the quantitative methoxylation of 3-bromo-4-hydroxybenzaldehyde with the recovery of pure methanol. Herein, the pivotal oxidation and methoxylation reactions are logically investigated and developed into two concise methodologies. As a green alternative, the approach holds significant value for the sustainable manufacturing of vanillin. the Partner Organisations 2014.
- Jiang, Jian-An,Chen, Cheng,Guo, Ying,Liao, Dao-Hua,Pan, Xian-Dao,Ji, Ya-Fei
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supporting information
p. 2807 - 2814
(2014/05/06)
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- Sodium lauryl sulfate-catalyzed oxidative chlorination of aromatic compounds
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Chlorination of commercially important aromatic compounds using sodium chloride as chlorine source and sodium periodate as oxidant in acidic medium catalyzed by sodium lauryl sulfate (SLS) led to the chloro-substituted aromatics in good yields and purity. Addition of sodium lauryl sulfate led to increased chlorination rate, better yield, excellent purity, and better quality of end product. The advantages of the present method are greater yield, excellent purity, and shorter reaction time at room temperature. Also dichlorinated product can be obtained by increasing the amount of sodium chloride and sodium periodate at slightly higher temperature (40C).
- Mahajan, Tanu,Kumar, Lalit,Dwivedi, K.,Agarwal, D. D.
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p. 3655 - 3663,9
(2020/08/31)
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- Aromatic substitution in ball mills: Formation of aryl chlorides and bromides using potassium peroxomonosulfate and NaX
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Aryl chlorides and bromides are formed from arenes in a ball mill using KHSO5 and NaX (X = Cl, Br) as oxidant and halogen source, respectively. Investigation of the reaction parameters identified operating frequency, milling time, and the number of milling balls as the main influencing variables, as these determine the amount of energy provided to the reaction system. Assessment of liquid-assisted grinding conditions revealed, that the addition of solvents has no advantageous effect in this special case. Preferably activated arenes are halogenated, whereby bromination afforded higher product yields than chlorination. Most often reactions are regio- and chemoselective, since p-substitution was preferred and concurring side-chain oxidation of alkylated arenes by KHSO5 was not observed. The Royal Society of Chemistry.
- Schmidt, Robert,Stolle, Achim,Ondruschka, Bernd
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p. 1673 - 1679
(2013/02/22)
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- Topical anti-inflammatory activity of boropinic acid and its natural and semi-synthetic derivatives
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Boropinic acid is a natural isopentenyloxycinnamic acid extracted from the aerial parts of Boronia pinnata Sm. (Rutaceae) with soybean 5-lipoxygenase inhibitory activity. In this paper the topical anti-inflammatory activity of boropinic acid and some of its natural and semi-synthetic derivatives was evaluated using the Croton oil ear test in mice as a model of acute inflammation. Some of the tested compounds (15, 17, 19, 20) revealed an effect comparable (ID50 = 0.18 ÷ 0.72 μmol/cm2) to that of the reference drug indomethacin (ID50 = 0.23 μmol/cm 2), a non-steroidal anti-inflammatory drug.
- Epifano, Francesco,Sosa, Silvio,Tubaro, Aurelia,Marcotullio, M. Carla,Curini, Massimo,Genovese, Salvatore
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supporting information; experimental part
p. 769 - 772
(2011/03/18)
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- INHIBITORS OF ACETYL-COA CARBOXYLASE
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The present invention relates to compounds that act as acetyl-CoA carboxylase (ACC) inhibitors. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.
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Page/Page column 35
(2010/11/17)
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- INHIBITORS OF ACETYL-COA CARBOXYLASE
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The present invention relates to compounds that act as acetyl-CoA carboxylase (ACC) inhibitors. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.
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Page/Page column 55
(2010/11/17)
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- 1, 2 DISUBSTITUTED HETEROCYCLIC COMPOUNDS
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1,2-disubstituted heterocyclic compounds which are inhibitors of phosphodiesterase 10 are described. Also described are processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of mammals, including human(s) for central nervous system (CNS) disorders and other disorders which may affect CNS function. Among the disorders which may be treated are neurological, neurodegenerative and psychiatric disorders including, but not limited to, those associated with cognitive deficits or schizophrenic symptoms.
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Page/Page column 113
(2010/01/30)
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- An improved solid-phase methodology for the synthesis of putative hexa- and heptapeptide intermediates in vancomycin biosynthesis
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The biosynthesis of the vancomycin aglycone involves three oxidative phenol coupling reactions, each catalyzed by a discrete cytochrome P450-like enzyme. Studies on the mechanism and specificity of the enzyme (called OxyB) catalyzing the first coupling, require access to suitable linear peptide precursors, each conjugated as a thioester to a peptide carrier domain of the vancomycin non-ribosomal peptide synthetase. An efficient route to representative free linear peptides is described here. The method makes use of Alloc-chemistry during solid-phase assembly of the peptide backbone, but importantly and in contrast to earlier efforts, largely avoids the use of amino acid side chain protecting groups. In this way, the target linear peptides can be released directly from the solid support under very mild conditions. The Royal Society of Chemistry 2005.
- Li, Dong Bo,Robinson, John A.
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p. 1233 - 1239
(2007/10/03)
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- Cdk inhibitors having 3-hydroxychromen-4-one structure
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The present invention relates to a novel 3-hydroxychromen-4-one derivative of formula (1), pharmaceutically acceptable salt, hydrate, solvate or isomer thereof which is useful as an inhibitor for Cyclin Dependent Kinase (“CDK”); to a process for preparing the compound of formula (1); and to a composition for suppression or treatment of cancer and diseases induced by cell proliferation such as inflammation, angiostenosis, angiogenesis, etc. comprising the compound of formula (1) as an active component together with pharmaceutically acceptable carriers.
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- Imidazopyridinone derivatives and their use as phosphodiesterase inhibitors
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A compound (Ia): wherein the variables are defined in the specification, its prodrug or a pharmaceutically acceptable salt thereof useful in the treatment of angina, hypertension etc.
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- Syntheses of chlorinated bisbibenzyls from bryophytes
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Chlorinated bisbibenzyls of the isoplagiochin type detected in different bryophyte species were synthesized by an efficient and flexible unit construction system making extensive use of Suzuki and Wittig protocols.
- Speicher, Andreas,Kolz, Juergen,Sambanje, Rufino Paulino
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p. 2503 - 2512
(2007/10/03)
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- Prodrugs of anthracyclines for use in antibody-directed enzyme prodrug therapy
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A series of new prodrugs of daunorubicin and doxorubicin which are candidates for antibody-directed enzyme prodrug therapy (ADEPT) is reported. These compounds (25a,b,c and 32a,b,c) have been designed to generate cytotoxic drugs after activation with β-gl
- Florent, Jean-Claude,Dong, Xia,Gaudel, Gilbert,Mitaku, Sofia,Monneret, Claude,Gesson, Jean-Pierre,Jacquesy, Jean-Claude,Mondon, Martine,Renoux, Brigitte,Andrianomenjanahary, Solo,Michel, Sylvie,Koch, Michel,Tillequin, Fran?ois,Gerken, Manfred,Czech, Joerg,Straub, Rainer,Bosslet, Klaus
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p. 3572 - 3581
(2007/10/03)
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- Baker's yeast mediated enantiospecific synthesis of anti-(2R,3R)-p-chloro-3-hydroxytyrosine: An α-amino-β-hydroxy acid of vancomycin
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Baker's yeast mediated reduction of α-azido-β-keto ester lead to reduction of the carbonyl group with high enantiospecificity and diastereoselectivity at low pH (4.0, e.e. >99%, d.e. 79%). At pH ~7, although the enantioselectivity is maintained, the diastereoselectivity is lost.
- Fadnavis,Vadivel, S. Kumara,Sharfuddin,Bhalerao
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p. 4003 - 4006
(2007/10/03)
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- An expeditious approach for the synthesis of β-hydroxy aryl α-amino acids present in vancomycin
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Stereoselective synthesis of the β-hydroxyaryl amino acids which constitute C and E rings of vancomycin is described making use of benzylic oxidation and asymmetric dihydroxylation as the key steps.
- Rama Rao,Chakraborty,Laxma Reddy,Srinivasa Rao
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p. 5043 - 5046
(2007/10/02)
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- Synthesis and Spectroscopic Data of Chlorinated 4-Hydroxybenzaldehydes
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All chlorinated 4-hydroxybenzaldehydes including three hitherto unknown compounds have been synthesized from chlorinated phenols by applying the Reimer-Tiemann method. (1)H NMR, (13)C NMR, and mass-spectral data on all compounds are reported.
- Knuutinen, Juha S.,Kolehmainen, Erkki T.
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p. 139 - 141
(2007/10/02)
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