- Regio- and Stereoselective Chlorocyanation of Alkynes
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A variety of terminal and internal alkynes were converted regio- and stereoselectively into (Z)-3-chloroacrylonitriles by treatment with BCl3 in the presence of stoichiometric amounts of imidazolium thiocyanates. These products could be readily functionalized to provide useful building blocks, thus demonstrating the synthetic value of the method. Preliminary mechanistic studies suggest initial activation of the cationic thiocyanate by the Lewis acid, followed by electrophilic attack of the alkyne. The syn addition of a chloride to the vinyl cation intermediate and final elimination of the thiourea unit afford the desired chloroacrylonitriles.
- Barrado, Alejandro G.,Zieliński, Adam,Goddard, Richard,Alcarazo, Manuel
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Read Online
- Novel benzenesulfonamide-bearing pyrazoles and 1,2,4-thiadiazoles as selective carbonic anhydrase inhibitors
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Two series comprising 20 novel benzenesulfonamides bearing thioureido-linked pyrazole 8 and amino-1,2,4-thiadiazole 10 were synthesized and assayed as human carbonic anhydrase (hCA) inhibitors against isoforms I and II as well as the tumor-associated isof
- Kumar, Rajiv,Kumar, Amit,Ram, Sita,Angeli, Andrea,Bonardi, Alessandro,Nocentini, Alessio,Gratteri, Paola,Supuran, Claudiu T.,Sharma, Pawan K.
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- Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions
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A one pot synthesis of β-ketonitriles from readily accessible 3-chloropropenals using economically benign iodine, aqueous ammonia and sodium hydroxide solution, employing mild reaction conditions have been described. This report presents a convenient, inexpensive, highly toxic-matter-free and eco-friendly approach for β-ketonitriles.
- Sharma, Pawan K.,Kumar, Rajiv,Ram, Sita,Chandak, Navneet
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supporting information
p. 1847 - 1856
(2021/04/26)
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- Design, Synthesis, and Biological Evaluation of 6-Substituted Thieno[3,2- d]pyrimidine Analogues as Dual Epidermal Growth Factor Receptor Kinase and Microtubule Inhibitors
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The clinical evidence for the success of tyrosine kinase inhibitors in combination with microtubule-targeting agents prompted us to design and develop single agents that possess both epidermal growth factor receptor (EGFR) kinase and tubulin polymerization inhibitory properties. A series of 6-aryl/heteroaryl-4-(3′,4′,5′-trimethoxyanilino)thieno[3,2-d]pyrimidine derivatives were discovered as novel dual tubulin polymerization and EGFR kinase inhibitors. The 4-(3′,4′,5′-trimethoxyanilino)-6-(p-tolyl)thieno[3,2-d]pyrimidine derivative 6g was the most potent compound of the series as an antiproliferative agent, with half-maximal inhibitory concentration (IC50) values in the single- or double-digit nanomolar range. Compound 6g bound to tubulin in the colchicine site and inhibited tubulin assembly with an IC50 value of 0.71 μM, and 6g inhibited EGFR activity with an IC50 value of 30 nM. Our data suggested that the excellent in vitro and in vivo profile of 6g may be derived from its dual inhibition of tubulin polymerization and EGFR kinase.
- Romagnoli, Romeo,Prencipe, Filippo,Oliva, Paola,Baraldi, Stefania,Baraldi, Pier Giovanni,Schiaffino Ortega, Santiago,Chayah, Mariem,Kimatrai Salvador, Maria,Lopez-Cara, Luisa Carlota,Brancale, Andrea,Ferla, Salvatore,Hamel, Ernest,Ronca, Roberto,Bortolozzi, Roberta,Mariotto, Elena,Mattiuzzo, Elena,Viola, Giampietro
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supporting information
p. 1274 - 1290
(2019/01/30)
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- One-pot synthesis of 2-substituted thieno[3,2-b]indoles from 3-aminothiophene-2-carboxylates through in situ generated 3-aminothiophenes
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A convenient protocol for one-pot synthesis of thieno[3,2-b]indoles, bearing aromatic, thien-2-yl or styryl fragments at C-2 position, from easily accessible 5-substituted 3-aminothiophene-2-carboxylates using the Fischer indolization reaction, was develo
- Irgashev, Roman A.,Steparuk, Alexander S.,Rusinov, Gennady L.
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supporting information
(2019/09/30)
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- 3-halo-3-aryl acrylonitrile and preparation method thereof
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The invention discloses 3-halo-3-aryl acrylonitrile and a preparation method thereof. The method comprises the following steps: dissolving alkyne nitrile into a first substance comprising acetic acid,and adding alkaline metal halide salt to obtain a react
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Paragraph 0029; 0047-0049
(2018/05/16)
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- Direct synthesis of 3-halo-3-arylacrylonitriles from the addition of cyanoalkynes with alkaline metal halides
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An efficient synthesis of 3-halo-3-arylacrylonitrile is described from the direct addition between cyanoalkynes and inorganic alkaline metal halides such as LiCl, LiBr and KI in good to satisfactory yields. No transition metal is needed for the synthesis
- Guan, Zhipeng,Liu, Zhiwen,Shi, Wei,Chen, Hao
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supporting information
p. 3602 - 3606
(2017/08/23)
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- Exploring the chemical space of ureidothiophene-2-carboxylic acids as inhibitors of the quorum sensing enzyme PqsD from Pseudomonas aeruginosa
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Pseudomonas aeruginosa employs a quorum sensing (QS) communication system that makes use of small diffusible molecules. Among other effects, the QS system coordinates the formation of biofilm which decisively contributes to difficulties in the therapy of
- Sahner, J. Henning,Empting, Martin,Kamal, Ahmed,Weidel, Elisabeth,Groh, Matthias,B?rger, Carsten,Hartmann, Rolf W.
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supporting information
p. 14 - 21
(2015/04/22)
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- New Convenient Strategy for Annulation of Pyrimidines to Thiophenes or Furans via the One-pot Multistep Cascade Reaction of 1 H -Tetrazoles with Aliphatic Amines
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A versatile, convenient, efficient and high-yield synthetic method for 2-R3,R4-amino-5-R1-6-R2-thieno[2,3-d]pyrimidin-4(3H)-ones, 2-R3,R4-amino-5-R1-6-R2-thieno[3,2-d]pyrimidin-4(3H)-ones, and benzofuro[3,2-d]pyrimidin-4(3H)-ones preparation has been developed. The reaction proceeded without using solvents and included several steps. A variety of thieno[2,3-d]pyrimidine and thieno[3,2-d]pyrimidine derivatives with substituents of different nature were obtained in high yields from substituted alkyl 2-(1H-tetrazol-1-yl)thiophene-3-carboxylates, 3-(1H-tetrazol-1-yl)thiophene-2-carboxylates, and 3-(1H-tetrazol-1-yl)benzofuran-2-carboxylate after their treatment with aliphatic amines.
- Pokhodylo, Nazariy T.,Shyyka, Olga Ya.,Matiychuk, Vasyl S.,Obushak, Mykola D.
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p. 399 - 403
(2016/01/15)
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- SELECTIVE HDAC1 AND HDAC2 INHIBITORS
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Provided herein are compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with HDAC activity, particularly diseases or disorders that involve activity of HDAC1 and/or HDAC2. Such diseases include cancer, sickle-cell anemia, beta-thalassemia, and HIV.
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Paragraph 0241; 0242; 0243
(2014/05/20)
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- Facile and efficient one-pot procedure for thieno[2,3-e][1,2,3]triazolo[1, 5-a]pyrimidines preparation
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Base-catalyzed cycloaddition reactions of heterocyclic azides with activated nitriles were studied. Convenient, efficient, and high-yield synthetic method for thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidines preparation from available starting reagents without complicated protocols was elaborated. Such an approach allows creation of broad combinatorial libraries for drug discovery. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Pokhodylo, Nazariy T.,Shyyka, Olga Y.,Obushak, Mykola D.
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p. 1002 - 1006
(2014/03/21)
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- SUBSTITUTED 4-(SELENOPHEN-2(OR-3)-YLAMINO)PYRIMIDINE COMPOUNDS AND METHODS OF USE THEREOF
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Selenophene compounds of formula (I) are described herein. In the compounds of Formula (I), ring A is a 6-membered aromatic fused ring, optionally containing one, two or three nitrogen atoms; a 5-membered heteroaromatic fused ring; or a mono- or bicyclic
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Paragraph 0254; 0258
(2013/10/22)
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- Novel small molecule inhibitors targeting the "switch region" of bacterial RNAP: Structure-based optimization of a virtual screening hit
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Rising resistance against current antibiotics necessitates the development of antibacterial agents with alternative targets. The "switch region" of RNA polymerase (RNAP), addressed by the myxopyronins, could be such a novel target site. Based on a hit can
- Sahner, J. Henning,Groh, Matthias,Negri, Matthias,Haupenthal, J?rg,Hartmann, Rolf W.
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supporting information
p. 223 - 231
(2013/10/01)
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- Continuous-flow preparation and use of β-chloro enals using the Vilsmeier reagent
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The Vilsmeier reagent is used in the preparation of a wide variety of heterocycles, such as pyrazoles, via formation of β-chloroacrolein intermediates. However, use of this extremely reactive reagent on large scale requires special precautions to avoid potentially dangerous exotherms. This article describes the safe preparation at room temperature of the Vilsmeier reagent under flow conditions for the formation of β-chloroacroleins and 3-formylchromones, as well as the use of these in multistep, continuous flow processes for the syntheses of β-acrylonitriles and polysubstituted pyrazoles.
- Pellegatti, Laurent,Buchwald, Stephen L.
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p. 1442 - 1448
(2012/10/29)
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- ANTI-CANCER DRUGS, AND USES RELATING FOR MALIGNANT MELANOMA AND OTHER CANCERS
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Selenopheno triazene analogs, their compositions, tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, and pharmaceutically acceptable salts and mixtures thereof are useful for the treatment of metastatic malignant melanoma and other cancers. The selenopheno triazene analogs have the general formulae (I) or (II): wherein the substituents R1, R2, R3, R6, and R7 are as described in the specification. Other cancers include which may be treated with these compounds include, but are not limited to, malignant melanoma, leukemia, lymphomas (Hodgkins and non-Hodgkins), sarcomas (Ewing's sarcoma), brain tumors, central nervous system (CNS) metastases, gliomas, carcinomas such as breast cancer, prostate cancer, lung cancer (small cell and non-small cell), colon cancer, pancreatic cancer, Head and Neck cancers and oropharyngeal squamous cell carcinoma.
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Page/Page column 43
(2010/11/17)
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- ANTI-CANCER DRUGS AND USES RELATING THERETO FOR METASTATIC MALIGNANT MELANOMA AND OTHER CANCERS
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The present invention discloses triazene analogs of the general formula (I) and formula (II), their tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, and pharmaceutically acceptable salts thereof for the metastatic malignant melanoma and other cancers including but not limited to lymphomas, sarcomas, carcinomas, and gliomas. The invention further discloses a process for the preparation of the above said triazene analogs of formula (I) and formula (II), and their pharmaceutically acceptable compositions.
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Page/Page column 33
(2010/04/06)
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- ANTI-CANCER DRUGS AND USES RELATING THERETO FOR METASTATIC MALIGNANT MELANOMA AND OTHER CANCERS
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The present invention discloses triazene analogs of the general formula (I) and formula (II), their tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, and pharmaceutically acceptable salts thereof for the metastatic malignant melanoma and other cancers including but not limited to lymphomas, sarcomas, carcinomas, and gliomas. The invention further discloses a process for the preparation of the above said triazene analogs of formula (I) and formula (II), and their pharmaceutically acceptable compositions.
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Page/Page column 14
(2010/04/23)
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- Synthesis of a novel series of thieno[3,2-d]pyrimidin-4-(3H)-ones
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2-Aminothieno[3,2-d]pyrimidin-4-ones were synthesized in one step by condensation of 3-amino(benzo)thiophene car-boxylate with chloroformamidine hydrochloride. Georg Thieme Verlag Stuttgart.
- Abdillahi, Ismail,Kirsch, Gilbert
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scheme or table
p. 1428 - 1430
(2010/10/03)
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- Synthesis of selenophene analogues of the tacrine series: Comparison of classical route and microwave irradiation
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New 3-amino-2-selenophenecarbonitriles condensed with cyclanones to afford, in one step, analogues of Tacrine. A comparison between classical heating and microwave irradiation for the Friedlaender condensation is presented. Georg Thieme Verlag Stuttgart.
- Thomae, David,Kirsch, Gilbert,Seck, Pierre
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scheme or table
p. 1600 - 1606
(2009/04/03)
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- Synthesis and biological evaluation of 2-(3′,4′,5′- trimethoxybenzoyl)-3-amino 5-aryl thiophenes as a new class of tubulin inhibitors
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2-(3′,4′,5′-Trimethoxybenzoyl)-3-amino-5-aryl/heteroaryl thiophene derivatives were synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. SARs were elucidated with various substitutions on
- Romagnoli, Romeo,Baraldi, Pier Giovanni,Remusat, Vincent,Carrion, Maria Dora,Lopez Cara, Carlota,Preti, Delia,Fruttarolo, Francesca,Pavani, Maria Giovanna,Aghazadeh Tabrizi, Mojgan,Tolomeo, Manlio,Grimaudo, Stefania,Balzarini, Jan,Jordan, Mary Ann,Hamel, Ernest
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p. 6425 - 6428
(2007/10/03)
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- Synthesis of thiazolidinones and azetidinones from hydrazino thieno [3,2-d]pyrimidines as potential antimicrobial agents
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4-Hydrazino-6-phenylthieno [3,2-d] pyrimidine 5 on treatment with aromatic aldehydes yield 4-substituted-benzalhydrazino-6-phenylthieno [3,2-d] pyrimidine 6a-k, which on cyclisation with thioglycolic and thiolactic acid afford corresponding 2-aryl-3-N-(6′
- Shah, Manish,Parikh, Khyati,Parekh, Hansa
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- Synthesis of some 2-substituted-6-phenyl- and 7-phenyl-thienopyrimidin-4(3H)-ones
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The title compounds, 7a-j and 8a-c, have been prepared through cyclocondensation of the corresponding thiophene o-aminoesters (5a and 5b) with a variety of nitriles in the presence of dry hydrogen chloride gas.
- Shishoo, C. J.,Pathak, U. S.,Jain, K. S.,Devani, I. T.,Chhabria, M. T.
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p. 436 - 440
(2007/10/02)
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- A Simple Synthesis of β-Chlorocinnamonitriles by a Modified Vilsmeier-Haack-Arnold-Reaction
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A simple one-pot synthesis of β-chloro-cinnamonitriles 2 can be achieved by treating acetyl arenes 1 first with formamide chlorides and subsequently with hydroxyl amine hydrochloride.The formamide chlorides used are conveniently prepared from an excess of
- Liebscher, Juergen,Neumann, Bernd,Hartmann, Horst
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p. 915 - 918
(2007/10/02)
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