- Acid activated montmorillonite K-10 mediated intramolecular acylation: Simple and convenient synthesis of 4-chromanones
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3-Aryloxyproionic acids undergo intramolecular cyclization in the presence of AA.Mont.K-10 in toluene under reflux for 30–45 min in good to excellent yields. Phenyl ring bearing various substituents at the ortho, meta, para positions undergo this cyclization reaction. This method involves simple work up and amenable for large scale preparations. The heterogeneous acid treated catalyst can be regenerated and used for up to three cycles with minimum loss of activity.
- Begum, Ayisha F.,Balasubramanian, Kalpattu K.,Shanmugasundaram, Bhagavathy
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supporting information
(2021/09/13)
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- 2-AMINO-1,3,4-THIADIAZINE AND 2-AMINO-1,3,4-OXADIAZINE BASED ANTIFUNGAL AGENTS
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The invention provides a compound which is a diazine of formula (I) or a tautomer thereof, or a pharmaceutically acceptable salt thereof, for use as an antifungal agent: (I) wherein X, N', C', A and E are as defined herein. The invention also provides a compound of Formula (I) as defined herein.
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Page/Page column 81
(2017/02/09)
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- Hydrated ferric sulfate-catalyzed reactions of indole with aldehydes, ketones, cyclic ketones, and chromanones: Synthesis of bisindoles and trisindoles
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Hydrated ferric sulfate [Fe2(SO4)3·xH2O] has been found to be an efficient catalyst for condensation of bisindoles or trisindoles with aliphatic or aryl aldehydes and ketones including methyl and ethyl-alkyl ketones, methyl aryl ketones, cyclic ketones, and 4-chromanones in 19–96% yields. Trisindoles and 2,2'-alkylidenebisindoles were obtained from indole-3-carbaldehydes or 3-methylindole in 72–84% yields. A total of 43 substrates was employed, giving 33 bisindoles, 3 trisindoles, and one 2:2 product; seventeen of these are new. The best results were obtained from heating ethanolic suspensions, with Fe2(SO4)3·xH2O loaded at 60 mg per mmol of electrophiles. The reaction times were typically 1–4 h, while hindered electrophiles required 8–24 h. These conditions were strong enough to promote 2:1 condensation of indole with substrates without forming higher-order byproducts, with few exceptions. This strategy features tolerance by the catalyst of a wide range of functional groups, readily available starting materials, simple operation, mild reaction conditions, and is environmentally friendly.
- Noland, Wayland E.,Kumar, Honnaiah Vijay,Flick, Grant C.,Aspros, Cole L.,Yoon, Jong Hyeon,Wilt, Andre C.,Dehkordi, Nasim,Thao, Sheng,Schneerer, Andrew K.,Gao, Siming,Tritch, Kenneth J.
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p. 3913 - 3922
(2017/06/13)
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- Efficient and rapid synthesis of phenolic analogs of 4-phenylbutanoic acid using microwave-assisted Michael addition as a key reaction
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ABSTRACT: The addition of phenols to acrylonitrile in the presence of aqueous benzyltrimethylammonium hydroxide or tetramethylammonium hydroxide under microwave irradiation yielded the corresponding Michael adducts. The obtained adducts were easily transformed to phenolic analogs of 4-phenylbutanoic acids via the hydrolysis of nitrile groups.
- Iida, Hirokazu,Akatsu, Yusuke,Mizukami, Kazushi,Natori, Sho,Matsukawa, Minako,Takahashi, Kie
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supporting information
p. 581 - 585
(2016/07/06)
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- Synthesis, evaluation and in silico molecular modeling of pyrroyl-1,3,4-thiadiazole inhibitors of InhA
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Enoyl acyl carrier protein reductase (ENR) is an essential type II fatty acid synthase (FAS-II) pathway enzyme that is an attractive target for designing novel antitubercular agents. Herein, we report sixty-eight novel pyrrolyl substituted aryloxy-1,3,4-thiadiazoles synthesized by three-step optimization processes. Three-dimensional quantitative structure-activity relationships (3D-QSAR) were established for pyrrolyl substituted aryloxy-1,3,4-thiadiazole series of InhA inhibitors using the comparative molecular field analysis (CoMFA). Docking analysis of the crystal structure of ENR performed by using Surflex-Dock in Sybyl-X 2.0 software indicates the occupation of pyrrolyl substituted aryloxy 1,3,4-thiadiazole into hydrophobic pocket of InhA enzyme. Based on docking and database alignment rules, two computational models were established to compare their statistical results. The analysis of 3D contour plots allowed us to investigate the effect of different substituent groups at different positions of the common scaffold. In vitro testing of ligands using biological assays substantiated the efficacy of ligands that were screened through in silico methods.
- Joshi, Shrinivas D.,More, Uttam A.,Koli, Deepshikha,Kulkarni, Manoj S.,Nadagouda, Mallikarjuna N.,Aminabhavi, Tejraj M.
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p. 151 - 167
(2015/03/30)
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- Design and synthesis of HIV-1 protease inhibitors for a long-acting injectable drug application
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The design and synthesis of novel HIV-1 protease inhibitors (PIs) (1-22), which display high potency against HIV-1 wild-type and multi-PI-resistant HIV-mutant clinical isolates, is described. Lead optimization was initiated from compound 1, a Phe-Phe hydroxyethylene peptidomimetic PI, and was directed towards the discovery of new PIs suitable for a long-acting (LA) injectable drug application. Introducing a heterocyclic 6-methoxy-3-pyridinyl or a 6-(dimethylamino)-3-pyridinyl moiety (R3) at the para-position of the P1′ benzyl fragment generated compounds with antiviral potency in the low single digit nanomolar range. Halogenation or alkylation of the metabolic hot spots on the various aromatic rings resulted in PIs with high stability against degradation in human liver microsomes and low plasma clearance in rats. Replacing the chromanolamine moiety (R1) in the P2 protease binding site by a cyclopentanolamine or a cyclohexanolamine derivative provided a series of high clearance PIs (16-22) with EC50s on wild-type HIV-1 in the range of 0.8-1.8 nM. PIs 18 and 22, formulated as nanosuspensions, showed gradual but sustained and complete release from the injection site over two months in rats, and were therefore identified as interesting candidates for a LA injectable drug application for treating HIV/AIDS.
- Kesteleyn, Bart,Amssoms, Katie,Schepens, Wim,Hache, Geerwin,Verschueren, Wim,Van De Vreken, Wim,Rombauts, Klara,Meurs, Greet,Sterkens, Patrick,Stoops, Bart,Baert, Lieven,Austin, Nigel,Wegner, J?rg,Masungi, Chantal,Dierynck, Inge,Lundgren, Stina,J?nsson, Daniel,Parkes, Kevin,Kalayanov, Genadiy,Wallberg, Hans,Rosenquist, ?sa,Samuelsson, Bertil,Van Emelen, Kristof,Thuring, Jan Willem
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p. 310 - 317
(2013/02/25)
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- Chroman Compound, Processes for Its Preparation, and Its Pharmaceutical Use
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The present invention provided a chroman compound, the method of its preparation and pharmaceutical applications. The compound are represented by formula (I) and its pharmaceutical salt, where in :x is for O or S; n is for 2, 3 or 4; R1 is 6-situ or 7-situ halogen, C1-4alkyl, C1-4alkyoxyl, benzyloxy, acylamino; R2 is nitrogen-containing pentatomic or hexahydric substituted heterocyclic ring. The compound is useful to prepare anti-arrhythmic drugs, the reaction conditions of the method are mild, the raw material are plenty and easy to be obtained, and the operation and post-treatment are simple.
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Page/Page column 7
(2008/06/13)
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- A New Class of Antiarrhythmic Agents: Mannich Bases of 3,4-Dihydro-1-benzoxepin-5(2H)-ones and Related Compounds
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Mannich bases derived from 3,4-dihydro-1-benzoxepin-5(2H)-ones, chromanones and 6,7,8,9-tetrahydrobenzocyclohepten-5(H)-one have been synthesised and shown to possess marked antiarrhythmic activity; 3,4-dihydro-7-methyl-4-(1-piperidinomethyl)- and 3,4-dih
- Khanna, J. M.,Tandon, V. K.,Kar, K.,Sur, R. N.
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- NOUVEAUX DERIVES DE LA BENZOPYRANNONE-4, A ACTIVITES ANALGESIQUE, ANTI-INFLAMMATOIRE ET ANTIAGREGANTE PLAQUETTAIRE
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A series of 35 new derivatives of 3-benzylidene benzopyran-4-one carboxylic acid was synthesized; their antiinflammatory and analgesic activities were investigated and compared with those of acetylsalicylic acid, phenylbutazone, ketoprofene and glafenine.Among these compounds, four were found to be more potent than the references compounds in tests of antiinflammatory and analgesic activity.Seven compounds were tested on rat blood platelet aggregation induced by ADP.From these tests, HD-039, HD-041, HD-044 and HD-049 appear to be promising antiinflammatory, analgesic and anticlotting agents, although this original series shows little structural analogy with classical non-steroidal antiinflammatory agents.
- Darmanaden, R.,Dhanutirto, H.,Castel, J.,Loubatiere, J.,Flandre, O.
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p. 876 - 887
(2007/10/02)
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- The Synthesis of 4-Methylcyclohexa-2,5-dienones from Phenols
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4-Alkyl phenols have been converted by a known sequence into 2-aryloxyisobutyric acids and thence, by bromination at the 4-position of the aromatic ring with concomitant intramolecular lactone formation, into masked 4-alkyl-4-bromocyclohexa-2,5-dienones.Reaction with lithium dimethylcuprate, as a model for other lithium dialkylcuprates, replaces the bromine by a methyl group.Hydrolytic demasking gives 4-alkyl-4-methylcyclohexa-2,5-dienones.The method should allow the general synthesis of 4-alkylated cyclohexa-2,5-dienones from phenols via a nucleophilic alkylation step.This contrasts with an existing route which uses electrophilic alkylation of phenols or phenoxide ions by a restricted range of reactive alkylating agents.
- Islam, M. Majharul,Waring, Anthony J.
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p. 768 - 783
(2007/10/02)
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