- Synthesis, Antiviral Activity, and Structure–Activity Relationship of 1,3-Benzodioxolyl Pyrrole-Based Entry Inhibitors Targeting the Phe43 Cavity in HIV-1 gp120
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The pathway by which HIV-1 enters host cells is a prime target for novel drug discovery because of its critical role in the life cycle of HIV-1. The HIV-1 envelope glycoprotein gp120 plays an important role in initiating virus entry by targeting the primary cell receptor CD4. We explored the substitution of bulky molecular groups in region I in the NBD class of entry inhibitors. Previous attempts at bulky substituents in that region abolished antiviral activity, even though the binding site is hydrophobic. We synthesized a series of entry inhibitors containing the 1,3-benzodioxolyl moiety or its bioisostere, 2,1,3-benzothiadiazole. The introduction of the bulkier groups was well tolerated, and despite only minor improvements in antiviral activity, the selectivity index of these compounds improved significantly.
- Curreli, Francesca,Belov, Dmitry S.,Ahmed, Shahad,Ramesh, Ranjith R.,Kurkin, Alexander V.,Altieri, Andrea,Debnath, Asim K.
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Read Online
- Montmorillonite clay catalysis. Part 14. A facile synthesis of 2-substituted and 2,2-disubstituted 1,3-benzodioxoles
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A series of 2-substituted and 2,2-disubstituted 1,3-benzodioxoles have been synthesised by reaction of catechol and pyrogallol with corresponding aldehydes and ketones catalysed by montmorillonite KSF or K-10. The reactions are completed within 2.7-24 h to give satisfactory yields. Ketones give better yields than aldehydes, although highly sterically hindered ketones and diaryl ketones fail to react at all.
- Li, Tong-Shuang,Li, Li-Jun,Lu, Bo,Yang, Feng
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Read Online
- Synthesis of Catecholate Ligands with Phosphonate Anchoring Groups
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New catecholate ligands containing protected phosphonate anchoring groups in the 4-position of the catecholate ring were synthesized. The catechol 4-diethoxyphosphorylbenzene-1,2-diol, (Etphoscat)H2, was prepared in three steps from pyrocatechol; whereas, the catechol 4-(diethoxyphosphorylmethyl)benzene-1,2-diol, (EtBnphoscat)H2, containing a methylene spacer between the catecholate ring and phosphonate anchor, was prepared from protocatechuic acid in six linear steps. Both catechol derivatives were further elaborated to their trimethylsilyl-protected counterparts to facilitate their binding to nanocrystalline metal oxides. Electronic spectroscopy and cyclic voltammetry were used to probe the electronic properties of the phosphonate-functionalized catecholates in charge-transfer complexes of the general formula (catecholate)Pd(pdi) (pdi = N,N′-bis(mesityl)phenanthrene-9,10-diimine). These studies show that attachment of the phosphonate anchor directly to the 4-position of the (Etphoscat)2- ligand significantly perturbs the donor ability of the catecholate ligand; however, incorporation of a single methylene spacer group in (EtBnphoscat)2- helps to isolate catecholate from the electron-withdrawing phosphonate group.
- Seraya, Elaine,Luan, Zhongyue,Law, Matt,Heyduk, Alan F.
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Read Online
- Synthesis of 4,5-dihydroxyphthalonitrile
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4,5-Dihydroxyphthalonitrile was synthesized from pyrocatechol in a simple way. The compound obtained is a convenient starting reagent for the preparation of 4,5-dialkoxyphthalonitriles.
- Ivanov,Svinareva,Tomilova,Zefirov
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Read Online
- Synthesis and biological activity of 2-carbomethoxy-3-catechol-8- azabicyclo[3.2.1]octanes
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Cocaine inhibits the dopamine transporter and the consequent elevation of dopamine is thought to contribute to the addictive properties of cocaine. Tropane analogues of cocaine, targeted to the dopamine transporter (DAT), are a significant focus of drug d
- Meltzer, Peter C.,McPhee, Mark,Madras, Bertha K.
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Read Online
- Quinoxaline compound, preparation method and application of quinoxaline compound in medicine
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The invention provides a quinoxaline compound, a preparation method and application of the quinoxaline compound in medicine, and particularly relates to a quinoxaline compound with PAR4 antagonistic activity, a preparation method of the quinoxaline compound, a pharmaceutical composition containing the quinoxaline compound and application of the quinoxaline compound. Specifically, the invention provides a compound shown as a general formula I and/or II or a tautomer or pharmaceutically acceptable salt thereof, a preparation method of the compound, and application of the compound or the tautomer or the pharmaceutically acceptable salt in medicines for preventing and/or treating thromboembolic diseases.
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Paragraph 0310-0313; 0324-0327
(2021/07/24)
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- Templated Chromophore Assembly on Peptide Scaffolds: A Structural Evolution
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The use of a template that bears pre-programmed receptor sites for selectively accommodating chromophores at given positions is an attractive approach for engineering artificial-light-harvesting systems. Indulging this line of thought, this work tackles the creation of tailored antenna architectures with yellow, red and blue chromophores, exploiting three dynamic covalent reactions simultaneously, namely disulfide exchange, acyl hydrazone, and boronic ester formations. The effect of various structural modifications, such as the chromophores as well as their spatial organization (distance, orientation, order) on the energy transfer within the antennas was studied by means of steady-state UV/Vis absorption and fluorescence spectroscopies. This systematic study allowed for a significant improvement of the energy-transfer efficiencies to a noticeable 22 and 15 % for the yellow and red donors, respectively, across the chromophores to the blue acceptor. Metadynamics simulations suggested that the conformational properties of the antennas are driven by intramolecular chromophoric stacking interactions that, upon forcing the α-helix to fold on itself, annul any effects deriving from the programming of the spatial arrangement of the receptor sides in the peptide backbone.
- Rocard, Lou,Wragg, Darren,Jobbins, Samuel Alexander,Luciani, Lorenzo,Wouters, Johan,Leoni, Stefano,Bonifazi, Davide
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supporting information
p. 16136 - 16148
(2018/10/15)
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- N-{[2-(PIPERIDIN-1-YL)PHENYL](PHENYL)METHYL}-2-(3-OXO-3,4-DIHYDRO-2H-1,4-BENZOXA ZIN-7-YL)ACETAMIDE DERIVATIVES AND RELATED COMPOUNDS AS ROR-GAMMA MODULATORS FOR TREATING AUTOIMMUNE DISEASES
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The present invention provides e.g. N-{[2-(piperidin-1-yl)phenyl] (phenyl)methyl}-2-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)acetamide derivatives and related compounds as ROR-gamma modulators for treating e.g. autoimmune diseases, autoimmune-related diseases, inflammatory diseases, metabolic diseases, fibrotic diseases or cholestatic diseases, such as e.g. arthitis and asthma.
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Page/Page column 68; 130
(2018/08/20)
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- Class of large ring heterocyclic compound restraining HCV and manufacturing and uses thereof
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The invention relates to a class of compounds that inhibit HCV. The compounds are represented by Formula A. The invention also relates to preparation and pharmaceutical use of the compounds.
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Paragraph 0291-0294
(2017/09/01)
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- Synthesis of a functionalized benzofuran as a synthon for salvianolic acid C analogues as potential LDL Antioxidants
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A palladium mediated synthesis of a common synthon for the syntheses of antioxidant analogues of naturally occurring salvianolic acids is presented. The synthetic route may be used to obtain analogues with a balanced lipophilicity/hydrophilicity which may
- López-Frías, Gabriela,Camacho-Dávila, Alejandro A.,Chávez-Flores, David,Zaragoza-Galán, Gerardo,Ramos-Sánchez, Víctor H.
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p. 8654 - 8665
(2016/09/04)
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- PROCESS FOR PRODUCTION OF HYDROXYTYROSOL USING ORGANOMETALLIC COMPOUNDS
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Disclosed is a process for the production of a 4-(2-hydroxyalkyl)-1,2-benzenediol, comprising the steps of (a) providing protected 1,2-benzenediol having the 1,2-hydroxyl groups protected, (b) halogenating the protected 1,2-benzenediol to obtain a protected 4-halo-1,2-benzenediol having the 1,2-hydroxyl groups protected, (c) reacting, in the presence of a metal or organometallic compound, the protected 4-halo-1,2-benzenediol to protected 4-(2-hydroxyalkyl)-1,2-benzenediol having the 1,2-hydroxyl groups protected, and (d) deprotecting the protected 4-(2-hydroxyalkyl)-1,2-benzenediol to obtain the 4-(2-hydroxyalkyl)-1,2-benzenediol. Also disclosed is the use of 1,2-benzenediol for the production of hydroxytyrosol.
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Page/Page column 13
(2012/02/02)
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- Microwave-assisted synthesis of 1,3-benzodioxole derivatives from catechol and ketones or aldehydes
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An efficient synthetic procedure for the preparation of a diverse library of 1,3-benzodioxoles was developed by applying controlled microwave heating in comparison with currently available conventional heating. Reactions were completed in less than 3 h. The isolation of product is simple, the isolated yields are good to excellent, and this method is applicable to large scale production.
- Pingali, Subramanya R.K.,Jursic, Branko S.
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experimental part
p. 4371 - 4374
(2011/09/19)
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- Cu(II)-impregnated sulfated MCM-41: An efficient and convenient protocol for the synthesis of 1,3-benzodioxoles
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An efficient synthesis of 1,3-benzodioxoles was achieved from catechol with different aldehydes and ketones using Cu(II) impregnated sulfated MCM-41 as an efficient and reusable catalyst. Copyright Taylor & Francis Group, LLC.
- Sivakumar,Ramesh,Lalitha
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experimental part
p. 91 - 93
(2011/03/23)
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- FUSED AMINO PYRIDINE AS HSP90 INHIBITORS
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The present invention relates to HSP90 inhibitors containing fused amino pyridine core that are useful as inhibitors of HSP90 and their use in the treatment of HSP90 related diseases and disorders such as cancer, an autoimmune disease, or a neurodegenerative disease.
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Page/Page column 58
(2008/12/08)
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- An efficient synthesis of 4,4′,5,5′-tetraiododibenzo-24-crown-8 and its highly conjugated derivatives
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4,4′,5,5′-Tetraiododibenzo-24-crown-8 (9), a practical building block, was prepared under efficient and mild reaction conditions starting from the simple starting material, catechol (1). Highly conjugated 4,4′,5,5′-tetraethynyldibenzo-24-crown-8 (10a,b) w
- Pak, Joshua J.,Mayo, Jaime L.,Shurdha, Endrit
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p. 233 - 237
(2007/10/03)
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- PROCESS FOR PREPARATION OF ESCULETIN COMPOUNDS, ESCULETIN COMPOUNDS AND INTERMEDIATES THEREOF, AND USE OF BOTH
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An esculetin compound, an intermediate thereof, a process for manufacturing an esculetin compound, and an antifungal composition for agriculture and horticulture and an herbicide comprising an esculetin compound or an intermediate thereof are provided. The process for manufacturing an esculetin compound is a low-cost, high-yield, and industrially practicable process, and comprises the following step.A process for manufacturing an esculetin compound of the formula (2): characterized by cyclizing a trihydroxybenzaldehyde compound of the formula (1): in an aprotic polar solvent in the presence of a weak base, with acetic anhydride or the like.
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Page/Page column 18-19
(2010/01/31)
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- An efficient and convenient method for preparation of 2,2-disubstituted and 2-monosubstituted 1,3-benzodioxoles from ketones and aldehydes with catechol catalysed by zro2/so42-
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The title compounds have been synthesised by reaction of catechol with ketones and aldehydes catalysed by ZrO2/SO42- solid superacid in high yields. Ketones gave better yields than aldehydes.
- Jin,Zhang,Wang,Guo,Li
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p. 289 - 291
(2007/10/03)
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- Cyclodextrin dimers as cleavable carriers of photodynamic sensitizers
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Several phthalocyanines carrying hydrophobic components have been synthesized and shown to bind to a group of cyclodextrin dimers with a carbon - carbon double bond in the linker. The complexes are soluble in water. On irradiation in the presence of oxygen, the singlet oxygen produced cleaves the olefinic linkers in the complexes, resulting in precipitation of the sensitizers. This process concentrates the sensitizers in the light beam, a process that has useful potential in photodynamic therapy.
- Baugh,Yang,Leung,Wilson,Breslow
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p. 12488 - 12494
(2007/10/03)
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- Synthesis of 2- and 2,2-Substituted 4,5-Benzo-1,3-dioxolanes
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Pyrocatechol reacts with carbonyl compounds in the presence of phosphorus trichloride to give corresponding 2- and 2,2-substituted 4,5-benzo-1,3-dioxolanes in high yields.
- Bikbulatov,Timofeeva,Zorina,Safiev,Zorin,Rakhmankulov
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p. 1805 - 1806
(2007/10/03)
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- HETEROCYCLIC HYDRAZIDE DERIVATIVES OF MONOCYCLIC BETA-LACTAM ANTIBIOTICS
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Antibacterial activity has been found in compounds of the formula. Compounds having the formula and pharmaceutically acceptable salts thereof, wherein: A is a bond or alkylene; Q completes a 5- or 6-membered saturated or unsaturated(including aromatic) heterocyclic ring having one or two, hetero atoms in the ring selected from nitrogen sulfur or oxygen; X is attached to an available carbon atom in the heterocyclic ring and is hydrogen or oxo; Y is attached to an available carbon atom in the heterocyclic ring and is hydrogen, amino, hydroxyl, halogen, carboxamide, nitrile, or carboxyl, except that Y is not carboxyl when the bicyclic ring completed by Q is 2-quinolyl, 3-quinolyl, or quinoxalyl; and the remaining symbols are as defined in the specification
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- Pesticidal heterocyclic compounds
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Compounds of the general formula: wherein R1 represents a hydrogen or halogen atom; R2 represents a halogen atom; R3 represents a hydrogen or halogen atom or an alkyl group; R4 and R5 each independent
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- Heteroaroylhydrazide derivatives of monocyclic beta-lactam antibiotics
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Compounds having the formula STR1 and pharmaceutically acceptable salts thereof and possessing antibacterial activity, and intermediates to compounds of formula I having the formula
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- Imidazole derivatives
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Tricyclic imidazole derivatives of the formula STR1 wherein R1 is 2-pyridyl optionally substituted by lower alkyl or lower alkoxy, n is the integer 0 or 1, R2 is hydrogen or lower alkyl, R3 and R4, independently, are hydrogen or lower alkyl, A is a group of the formula STR2 m is the integer 2 or 3, R5, R6, R7 and R8, independently, are hydrogen or lower alkyl, and R9 is hydrogen and R10 is hydrogen or lower alkyl or R9 and R10 taken together are oxo, provided that at least one of R3 and R4 is lower alkyl when A is a group of the formula and their pharmaceutically acceptable acid addition salts. The compounds of formula I inhibit gastric acid secretion and prevent the formation of gastric ulcers.
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- Mass Spectrometric Synthesis. II. The Reaction of Catechol With Acetone in a Protic Medium
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The reaction of catechol with acetone, carried out in the chemical ionization chamber of a VG ZAB 2F mass spectrometer and in the presence of a protic medium (CH5(1+)), leads to 2,2-dimethyl-1,3-benzodioxole.This has been proved by exact measurements and collisionally activated dissociation mass analyzed ion kinetic energy spectra.
- Podda, Gianni,Maccioni, Antonio,Daolio, Sergio,Traldi, Pietro
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p. 557 - 560
(2007/10/02)
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- Studies on the Synthesis of Heterocyclic Compounds. XI. Cleavage of 1,3-Benzodioxoles by Magnesium Bromide-Acetic Anhydride
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The cleavage reaction of some 1,3-benzodioxole derivatives with magnesium bromide and acetic anhydride has been studied.The reactions have been carried out in acetonitrile solution at room temperature.In all of the 1,3-benzodioxoles studied, the opening of the heterocyclic ring with formation of bromides, alkenes and their corresponding products of hydrolysis have been observed.The competitive electrophilic substitution on the benzene ring was very limited and was insignificant when a large excess of the cleavage reagent was used.The structures of newly prepared compounds have been determined by elemental analysis, spectroscopic data and comparison with authentic samples.
- Bonsignore, Leonardo,Fadda, Anna Maria,Loy, Giuseppe,Maccioni, Antonio,Podda, Gianni
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p. 703 - 707
(2007/10/02)
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- An Improved Method for the Synthesis of 2,2-disubstituted and 2-Monosubstituted 1,3-Benzodioxoles
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The reactions of catechol with ketones and aldehydes have been studied and convenient procedures have been developed for the preparation of the title compounds in high yields.These products undergo virtually quantitative nitration at position 5, thus providing a source of derivatives substituted in the benzene ring.
- Cole, Edward R.,Crank, George,Minh, H. T. Hai
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p. 675 - 680
(2007/10/02)
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- Dependence of Aryl Ether Acylation upon Lewis Acid Stoichiometry
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Acylation of alkyl aryl ethers has been observed to be uniquely dependent on the stoichiometry of the Friedel-Crafts catalyst.With 100 molpercent catalyst, acylation proceeds rapidly and in high yield; with large molar excesses of catalyst, the reaction is essentially completely arrested.This inhibition can be reversed by using sterically bulky alkyl groups which effectively prevent complexing between catalyst and aryl ether.Based on these observations, we have developed processes for regioselective intramolecular acylation of either a phenyl or an alkoxylated phenyl ring when both are present.
- Buckley, Thomas F.,Rapoport, Henry
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p. 3056 - 3062
(2007/10/02)
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