- Solvent-free synthesis of quinolone derivatives
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Quinolones can be prepared in a three step procedure from triethylorthoformate and activated methylene derivatives leading to alkoxymethylenemalonates followed by reaction with aromatic amines and finally a cyclization. All the reactions were carried out under solvent-free conditions possibly under microwave activation with benefits for the first step.
- Cernuchova, Petra,Vo-Thanh, Giang,Milata, Viktor,Loupy, Andre
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- 1,1'-Dicyano-2-substituted ethylenes : A new class of glucose uptake inhibitors in antifilarial chemotherapy
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Several 1,1'-dicyano-2-substituted ethylenes (2-16) were synthesized and evaluated for in vivo antifilarial activity. Some of the screened compounds showed significant antifilarial response against Acanthocheilonema viteae in rodents.
- Tewari, Swati,Chauhan,Bhaduri,Singh,Fatma, Nigar,Chatterjee,Srivastava
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- One Pot Synthesis of 3-Amino-1H-pyrazole-4-carbonitrile
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Condensation of malodinitrile with trimethoxymethan and aniline affords 3-anilino-2-cyanoacrylonitrile, which on treatment with hydrazine gives the title compound.Aniline can be recovered almost quantitatively. Keywords: Enaminonitrile; Amine exchange; Cyclisation
- Wolfbeis, Otto S.
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- An efficient synthesis of 3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one derivatives via an iminophosphorane
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The iminophosphorane (3), obtained from reaction of ethyl 3-amino-4-cyano-1-phenyl-1H-pyrrole-2-carboxylate (2) with triphenylphosphine, hexachloroethane, and triethylamine, reacted with aromatic isocyanates to give carbodiimides (4). Further reaction of
- He, Ping,Yan, Yan-Mei,Ding, Ming-Wu
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- Triflic acid-mediated N-heteroannulation of β-anilino-β-(methylthio)acrylonitriles: a facile synthesis of 4-amino-2-(methylthio)quinolines
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Various functionalised 4-amino-2-(methylthio)quinolines are synthesised through triflic acid-mediated N-heteroannulation of α-functionalized-β-anilino-β-(methylthio)acrylonitriles for the first time. The N-heteroannulation process is highly chemoselective and has mild reaction conditions. However, this process fails in the absence of the β-methylthio group in the acrylonitriles. In addition, a new double N-heteroannulation process is demonstrated to synthesise indolo[3,2-c]quinolines from non-heterocyclic precursors. Natural product isocryptolepine is synthesised in four steps from an acyclic precursor.
- Bandyopadhyay, Debashruti,Panigrahi, Adyasha,Peruncheralathan, S.,Radhakrishnan, Divya,Thirupathi, Annaram
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supporting information
p. 8544 - 8553
(2021/10/20)
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- Synthesis, biological evaluation, and molecular modeling of nitrile-containing compounds: Exploring multiple activities as anti-Alzheimer agents
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Based on the monoamine oxidase (MAO) inhibition properties of aminoheterocycles with a carbonitrile group we have carried out a systematic exploration to discover new classes of carbonitriles endowed with dual MAO and AChE inhibitory activities, and Aβ anti-aggregating properties. Eighty-three nitrile-containing compounds, 13 of which are new, were synthesized and evaluated. in vitro screening revealed that 31, a new compound, presented the best lead for trifunctional inhibition against MAO A (0.34 μM), MAO B (0.26 μM), and AChE (52 μM), while 32 exhibited a lead for selective MAO A (0.12 μM) inhibition coupled to AChE (48 μM) inhibition. Computational analysis revealed that the malononitrile group can find an advantageous position with the aromatic cleft and FAD of MAO A or MAO B. However, the total binding energy can be handicapped by an internal penalty caused by twisting of the ligand molecule and subsequent disruption of the conjugation (32 in MAO B compared to the conjugated 31). Conjugation is also important for AChE as well as the hydrophilic character of malononitrile that allows this group to be in close contact with the aqueous environment as seen for 83. Although the effect of 31 and 32 against Aβ1–42, was very weak, the effect of 63 and 65, and of the new compound 75, indicated that these compounds were able to disaggregate Aβ1–42 fibrils. The most effective was 63, a (phenylhydrazinylidene)propanedinitrile derivative that also inhibited MAO A (1.65 μM), making it a potential lead for Alzheimer's disease application.
- Silva, Daniel,Mendes, Eduarda,Summers, Eleanor J.,Neca, Ana,Jacinto, Ana C.,Reis, Telma,Agostinho, Paula,Bolea, Irene,Jimeno, M. Luisa,Mateus, M. Luisa,Oliveira-Campos, Ana M. F.,Unzeta, Mercedes,Marco-Contelles, José,Majekova, Magdalena,Ramsay, Rona R.,Carreiras, M. Carmo
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p. 215 - 231
(2019/09/03)
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- Pyrrolopyrimidine derivatives and purine analogs as novel activators of Multidrug Resistance-associated Protein 1 (MRP1, ABCC1)
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Multidrug resistance (MDR) is the main cause of diminished success in cancer chemotherapy. ABC transport proteins are considered to be one important factor of MDR. Besides P-glycoprotein (P-gp, ABCB1) and Breast Cancer Resistance Protein (BCRP, ABCG2), Mu
- Schmitt, Sven Marcel,Stefan, Katja,Wiese, Michael
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- Synthesis and biological evaluation of new tacrine analogues under microwave irradiation
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Efficient routes to various kinds of heterocycles incorporating the p-halophenyl moiety have been synthesized. Different pyrrole derivatives have been synthesized, as well, by Thorpe–Ziegler cyclization. Therefore, we synthesized different analogues of tacrine by Friedl?nder reaction of o-amino nitriles (pyrazolo, furano and pyrrolo) with different cycloalkanones. The use of microwave irradiation leads to shorter production times and high product conversion. These synthesized compounds were biologically evaluated by Ellman’s test on acetylcholinesterase inhibition.
- Alshareef, Hossa Fahad,Mohamed, Heba Abd El Hady,Salaheldin, Abdellatif Mohamed
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p. 732 - 738
(2017/08/09)
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- Pyrrolopyrimidine Derivatives as Novel Inhibitors of Multidrug Resistance-Associated Protein 1 (MRP1, ABCC1)
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Five series of pyrrolo[3,2-d]pyrimidines were synthesized and evaluated with respect to potency and selectivity toward multidrug resistance-associated protein 1 (MRP1, ABCC1). This transport protein is a major target to overcome multidrug resistance in cancer patients. We investigated differently substituted pyrrolopyrimidines using the doxorubicin selected and MRP1 overexpressing small cell lung cancer cell line H69 AR in a calcein AM and daunorubicin cell accumulation assay. New compounds with high potency and selectivity were identified. Piperazine residues at position 4 bearing large phenylalkyl side chains proved to be beneficial for MRP1 inhibition. Its replacement by an amino group led to decreased activity. Aliphatic and aliphatic-aromatic variations at position 5 and 6 revealed compounds with IC50 values in high nanomolar range. All investigated compounds had low affinity toward P-glycoprotein (P-gp, ABCB1). Pyrrolopyrimidines with small substituents showed moderate inhibition against breast cancer resistance protein (BCRP, ABCG2).
- Schmitt, Sven Marcel,Stefan, Katja,Wiese, Michael
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p. 3018 - 3033
(2016/05/19)
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- Oxidation of 2-cyanoprop-2-enethioamides with hydrogen peroxide
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Oxidation of (E)-3-aryl-2-cyanoprop-2-enethioamides with 32% H 2O2 under mild conditions gave (E)-3-aryl-2-cyano-1- iminioprop-2-ene-1-sulfenates in 70-88% yields. Under the conditions of the Radziszewski reaction (H2O2, 10% aqueous KOH) or upon prolonged treatment with H2O2, (E)-3-aryl-2-cyanoprop-2- enethioamides underwent transformations leading to complex mixtures of oxidation products. In some cases, 3-aryloxirane-2,2-dicarboxamides were isolated from those mixtures in low yields (2O2/KOH in ethanol afforded (arylaminomethylidene)malononitriles.
- Dotsenko,Krivokolysko,Shishkina,Shishkin
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p. 2082 - 2087
(2013/10/01)
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- Synthesis of new tacrine analogues from 4-amino-1H-pyrrole-3-carbonitrile
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An easy preparation of 4-amino-1H-pyrrole-3-carbonitrile derivatives and their transformation into new substituted pyrrolo[3,2-b]pyridines is described. The one-step transformation was carried out via Friedlaender reaction under microwave irradiation and
- Salaheldin, Abdellatif M.,Oliveira-Campos, Ana M. F.,Parpot, Pier,Rodrigues, Ligia M.,Oliveira, M. Manuel,Feixoto, Francisco P.
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scheme or table
p. 242 - 248
(2010/05/15)
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- REACTION OF 2,5-SUBSTITUTED 3,3,4,4-TETRACYANOPYRROLIDINES WITH ANILINES
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The ambiguity of the reaction of primary aromatic amines with 2,5-substituted 3,3,4,4-tetracyanopyrrolidines depending on conditions was shown: At room temperature 2-amino-1-R1-5-R-3,4,4-tricyano-2-pyrrolines are formed, while on heating-2-aryl
- Nasakin, O. E.,Lyshchikov, A. N.,Lukin, P. M.,Tafeenko, V. A.,Bulai, A. Kh.,Medvedev, S. V.
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p. 1124 - 1129
(2007/10/02)
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- Synthesis of 2-Substituted Pyrazolopyrimidines
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The reaction of 1-acetyl-2-phenylhydrazine with ethoxymethylenemalononitrile yielded propanedinitrile.Hydrolysis followed by annulation with methyl isocyanate provided a synthetic route to 2-phenylpyrazolo3,4
- Quinn, Ronald J.,Scammells, Peter J.,Kennard, Colin H.L.,Smith, Graham
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p. 1795 - 1801
(2007/10/02)
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- ACETALS OF LACTAMS AND ACID AMIDES. 41. ENAMINO AMIDES IN THE SYNTHESIS OF PYRIMIDINE DERIVATIVES
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The reaction of α-cyano-β-dimethylaminomethyleneacrylamide with arylamines was used to synthesize α-cyano-β-arylaminoacrylamides, which react readily with dimethylformamide diethylacetal to give the corresponding N-dimethylaminomethylene derivatives.The latter undergo cyclization to 1-aryl-5-cyano-4-pyrimidinones when they are heated in dimethylformamide or acetic anhydride and to pyrimidoquinolone derivatives when they are heated in glacial acetic acid.
- Ershov, L. V.,Kiselev, S. S.,Granik, V. G.
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p. 439 - 443
(2007/10/02)
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- β,β-Diacyl-enamine und -enole, 9. Zur Darstellung von Aminomethylenderivaten offenkettiger CH2-acider Verbindungen
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The reaction of a combination of primary or secondary aromatic or aliphatic amines with orthocarboxylic esters upon a variety of open-chain CH2-acidic molecules gives N-substituted aminoalkylidene derivatives.The method is highly recommended for methylene
- Wolfbeis, Otto S.
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p. 3471 - 3484
(2007/10/02)
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- Cyanoacrylates. Herbicidial and Photosynthetic Inhibitory Activity
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Various alkyl 3-ohenylamino-2-cyano- and 2-ethoxycarbonylacrylates and 3-phenylamino-2-cyanoacrylonitriles were synthesized and assayed as inhibitors of the Hill reaction in isolated pea chloroplast suspensions and as pre- and post-emergent herbicides on mustard and barnyard grass.Many of the compounds were potent Hill reaction inhibitors and several showed significant herbicidial activity.
- Huppatz, John L.,Phillips, John N.,Rattigan, Barbara M.
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p. 2769 - 2774
(2007/10/02)
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