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Journal articles on the topic '(amino-3 méthyl-2 tetrahydro-1,2,3,4)'

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Published: 4 June 2021

Last updated: 1 February 2022

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1

Khan, Ashraf Y., Nikhath Fathima, Mallikarjun B. Kalashetti, Noor Shahina Begum, and I. M. Khazi. "2-Amino-4-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile." Acta Crystallographica Section E Structure Reports Online 68, no. 10 (September 26, 2012): o3025. http://dx.doi.org/10.1107/s160053681204010x.

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2

Asiri, Abdullah M., Salman A. Khan, and M. Nawaz Tahir. "2-[(4-Chlorobenzylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile." Acta Crystallographica Section E Structure Reports Online 67, no. 9 (August 6, 2011): o2254. http://dx.doi.org/10.1107/s1600536811030704.

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3

Vasu, K. A. Nirmala, Deepak Chopra, M. D. Lakshman, and J. Saravanan. "2-[(E)-(4-Hydroxy-3-methoxybenzylidene)amino]-N-(2-methylphenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide." Acta Crystallographica Section C Crystal Structure Communications 64, no. 3 (February 23, 2008): o184—o186. http://dx.doi.org/10.1107/s0108270108001133.

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4

Kaur, Manpreet, Jerry P. Jasinski, Channappa N. Kavitha, H. S. Yathirajan, and K. Byrappa. "{2-[(4-Nitrobenzylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}(phenyl)methanone." Acta Crystallographica Section E Structure Reports Online 70, no. 6 (May 31, 2014): o738—o739. http://dx.doi.org/10.1107/s1600536814012185.

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In the title compound, C22H18N2O3S, disorder is found in the benzoyl group (AandB), as well as for four C atoms of the cyclohexene ring. Two orientations were modeled in a 0.583 (5):0.417 (5) ratio. The cyclohexene ring is in a distorted chair conformation. The dihedral angles between the mean plane of the thiophene ring and the 4-nitrobenzene and phenyl rings are 30.9 (8) and 64.8 (3) (A) and 62.4 (7)° (B). The mean planes of the 4-nitrobenzene and the phenyl rings are almost perpendicular to each other, with dihedral angles of 85.4 (1) (A) and 83.9 (8)° (B). An extensive array of weak C—H...O interactions consolidate molecules into a three-dimensional architecture, forming chains along [001] and [010] and layers parallel to (011).

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5

Anilkumar, G. N., M. K. Kokila, Puttaraja, S. Mohan, and K. S. Majunath Shetty. "N-(3-Chlorophenyl)-2-{[(1E)-(4-methylphenyl)methylene]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide." Acta Crystallographica Section E Structure Reports Online 61, no. 9 (August 12, 2005): o2841—o2843. http://dx.doi.org/10.1107/s1600536805024773.

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6

Shaibah, Mohammed A. E., Belakavadi K. Sagar, Hemmige S. Yathirajan, David B. Cordes, Alexandra M. Z. Slawin, and William T. A. Harrison. "Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates: a robust R_{2}^{2}(8) supramolecular motif (even when disordered)." Acta Crystallographica Section E Crystallographic Communications 75, no. 2 (January 8, 2019): 167–74. http://dx.doi.org/10.1107/s2056989018018224.

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The syntheses and structures of five molecular salts of protonated 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (C11H19N2S+) with different deprotonated carboxylic acids (4-methylbenzoic acid, 4-bromobenzoic acid, 3,5-dinitrobenzoic acid, fumaric acid and succinic acid) are reported, namely 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium 4-methylbenzoate, C11H19N2S+·C8H7O2 −, (I), 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium 4-bromobenzoate, C11H19N2S+·C7H4BrO2 −, (II), 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium 3,5-dinitrobenzoate, C11H19N2S+·C7H3N2O6 −, (III), bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium) fumarate, 2C11H19N2S+·C4H2O4 2−,(IV), and the 1:1 co-crystal of bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium) succinate and 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium hydrogen succinate 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine, 1.5C11H19N2S+·0.5C4H4O4 2−·0.5C4H5O4 −. 0.5C11H18N2S, (V). In every case, the cation protonation occurs at the N atom of the thiazole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methylene groups are disordered over two sets of sites). The C—N bond lengths of the nominal –NH+=C—NH2 fragment of the cation are indistinguishable, indicating a significant contribution of the –NH—C=N+H2 resonance form to the structure. The packing for (I)–(V) features a robust local R 2 2(8) loop motif in which the cation forms two near-linear N—H...O hydrogen bonds from the N+—H group and syn H atom of the amine group to the carboxylate group of an adjacent anion [(V) shows disorder of one of these bonds over N—H...O and N...H—O contributors but the same R 2 2(8) loop results for both disorder components]. The anti H atom of the –NH2 group also forms an N—H...O hydrogen bond, which results in [001] chains in (I) and (II), isolated centrosymmetric tetramers in (III) and [100] chains in (IV) and (V). Hirshfeld fingerprint plots and contact percentages for the different types of contacts of the cations are discussed.

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7

Anilkumar, G. N., M. K. Kokila, Puttaraja, S. Mohan, and K. S. Manjunath Shetty. "N-(2-Chlorophenyl)-2-{[(1E)-(4-methoxyphenyl)methylene]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide." Acta Crystallographica Section E Structure Reports Online 61, no. 9 (August 27, 2005): o3038—o3040. http://dx.doi.org/10.1107/s1600536805026413.

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8

Nesterov, Vladimir N., David J. Wiedenfeld, Svitlana V. Nesterova, and Mark A. Minton. "2-Amino-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile and 2-amino-7,7-dimethyl-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile." Acta Crystallographica Section C Crystal Structure Communications 60, no. 5 (April 21, 2004): o334—o337. http://dx.doi.org/10.1107/s0108270104006924.

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9

Youssif, Shaker, and Fatmah Agili. "One-pot Synthesis of Fused 2-Thiouracils: Pyrimidopyrimidines, Pyridopyrimidines and Imidazolopyrimidines." Zeitschrift für Naturforschung B 63, no. 7 (July 1, 2008): 860–64. http://dx.doi.org/10.1515/znb-2008-0709.

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Several 6-substitued-1-methyl-2,5,7,8-tetrahydro-2-thiopyrimido[4,5-d]pyrimidine-4-ones and ethyl 7-amino-5-aryl-1-methyl-4-oxo-1,2,3,4-tetrahydro-2-thiopyrido[2,3-d]pyrimidines-6-carboxylates were synthesized by treatment of 6-amino-1-methyl-2-thiouracil with primary amines and formalin (40%), and with ethyl 3-aryl-2-cyanoacrylate respectively. 8-Substituted-7-hydroxy-3- methyl-2-thioxanthines were synthesized by the treatment of 6-amino-1-methyl-5-nitroso-2-thiouracil with benzylidene-anilines. Elemental and spectral analyses were performed for the new compounds.

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10

Anilkumar, G. N., M. K. Kokila, Puttaraja, S. Mohan, and J. Saravanan. "N-(4-Fluorophenyl)-2-{[(1E)-(4-methoxyphenyl)methylene]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide." Acta Crystallographica Section E Structure Reports Online 63, no. 5 (April 4, 2007): o2077—o2079. http://dx.doi.org/10.1107/s1600536807012937.

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11

Vasu, K. A. Nirmala, Deepak Chopra, S. Mohan, and J. Saravanan. "3-Amino-2-methyl-5,6,7,8-tetrahydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one." Acta Crystallographica Section E Structure Reports Online 60, no. 7 (June 26, 2004): o1239—o1240. http://dx.doi.org/10.1107/s1600536804014862.

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12

Youssef, Ahmed Said Ahmed. "Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile and 6-amino-1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]pyrazole-5-carbonitrile with substituted benzylidenemalononitriles, α,β-acetylenic esters and ketones." Journal of Chemical Research 2009, no. 4 (April 2009): 214–17. http://dx.doi.org/10.3184/030823409x435874.

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Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile (1a) with substituted benzylidenemalononitriles gave 4-amino-2-(1-cyano-2-arylvinyl)benzothieno[2,3- d]pyrimidine derivatives (3) as ( E,Z)-mixtures and in one case (2c) as separated ( Z)- and ( E)-isomers. Similar treatment of 6-amino-1,4-dihydro-3-methyl-1,4-diphenyl-pyrano[2,3- c]pyrazole-5-carbonitrile (4) yielded similarly-formed pyrazolopyranopyrimidine derivatives (5a, b) as ( Z)-and ( E)-stereoisomers. Attempted acetylation of the aminobenzothienopyrimidines resulted in degradation of the pyrimidine ring and the formation of N-(3-cyano-4,5,6,7-tetrahydro[1]benzothien-2-yl)acetamide (1b). Treatment of 4 with acetylenic esters and ketones (6a-d) afforded the ( Z)-substituted enaminopyrano[2,3- c]pyrazole derivatives. Reacting 1a with aroyl phenyl acetylenes gave by Michael addition the enamino-ketones (8a-c).

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13

Smicius, Romualdas, Virginija Jakubkiene, Milda M. Burbuliene, Aiste Mikalainyte, and Povilas Vainilavicius. "Synthesis of 1-(6-Methyl-2,4-Dioxo-1,2,3,4-Tetrahydro-3-Pyrimidinyl)Acetyl-4-Alkyl(Aryl)Thiosemicarbazides and their Heterocyclisation to 1,2,4-Triazoles and 1,3,4-Thiadiazoles." Journal of Chemical Research 2002, no. 4 (April 2002): 170–72. http://dx.doi.org/10.3184/030823402103171555.

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5-(6-Methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)methyl-1,3,4-oxadiazole-2-thione reacts with amines to give 1-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)acetyl-4-alkyl(aryl)thiosemicarbazides, which on treatment with base or acid undergo cyclisation to 4-alkyl-1,2,4-triazole-2-thiones or 4-amino-1,3,4-thiadiazoles, respectively.

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14

Mahmud, Al, ME Halim, MK Ali, MA Kabir, K. Akhter, K. Jahan, and UKR Romman. "One pot synthesis of 2- amino-5-oxo-4-aryl-5, 6, 7, 8-tetrahydro- 4Hchromenes- 3-carboxilic acid ethyl esters." Bangladesh Journal of Scientific and Industrial Research 53, no. 1 (March 11, 2018): 35–40. http://dx.doi.org/10.3329/bjsir.v53i1.35908.

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Ethyl esters of 2-cyano-3-arylacrylic acid 1a-b ( a = 3- Br- C6H4, b= 4- OH- C6H4 ) reacted with 5, 5-dimethyl-1, 3-cyclohexane (2b, R = CH3) and 1c-d (c= 3- OH- C6H4, d= 3- NO2- C6H4 ) reacted with 1, 3-cyclohexanedione (2a, R = H) and 5, 5-dimethyl-1, 3-cyclohexanedione (2b, R=CH3) in the presence of alcoholic sodium ethoxide to give the corresponding ethyl esters of 2- amino- 7, 7- dimethyl-5-oxo-4-aryl-5, 6, 7, 8-tetrahydro- 4H- chromenes-3-carboxylic acid 3a-c, 3f and 2- amino-5-oxo-4-aryl-5, 6, 7, 8-tetrahydro- 4H- chromenes-3-carboxilic acid ethyl esters 3d-e. The structures of the compounds 3a-f were confirmed by their ultraviolet (UV), infrared (IR), 1H NMR, 13C NMR, mass spectra and elemental analyses.Bangladesh J. Sci. Ind. Res.53(1), 35-40, 2018

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15

Qu, Ying-Juan. "Crystal structure of 2-amino-4-(3-phenoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C22H18N2O3." Zeitschrift für Kristallographie - New Crystal Structures 231, no. 2 (June 1, 2016): 505–6. http://dx.doi.org/10.1515/ncrs-2015-0168.

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AbstractC22H18N2O3, triclinic, P1̅ (no. 2), a = 8.5476(10) Å, b = 8.7361(10) Å, c = 13.0076(12) Å, α = 80.085(8)°, β = 79.20(1)°, γ = 81.66(1)°, V = 933.43(18) Å3, Z = 2, Rgt(F) = 0.0582, wRref(F2) = 0.1886, T = 293 K.

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16

Chiriapkin, A. S., I. P. Kodonidi, and M. V. Larsky. "Targeted Synthesis and Analysis of Biologically Active Azomethine Derivatives of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide." Drug development & registration 10, no. 2 (May 29, 2021): 25–31. http://dx.doi.org/10.33380/2305-2066-2021-10-2-25-31.

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Introduction. Azomethine derivatives of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide are acyclic precursors of biologically active compounds derived from 5,6,7,8-tetrahydro-3H-benzoteopheno[2,3-d]pyrimidine-4-one. Examples of these groups of compounds with different pharmacological properties are given in the literature, but their cytostatic effect is mainly described. These data and the preparative availability allow us to judge the prospects for further study and molecular design in a number of azomethine derivatives of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide. Optimization of methods for the synthesis and analysis of substances of this series and the identification of structure-activity relationship are of considerable interest for medical chemistry and pharmaceutical science. The resulting leading compounds will allow us to further develop laboratory requirements for the synthesis of an active pharmaceutical substance.Aim. To make a predict, optimize the synthesis conditions and develop a method for high performance liquid chromatography (HPLC) analysis of pharmacologically active azomethine derivatives of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide.Materials and methods. The prediction of biological activity was carried out through the web resource PASS Online. The synthesis of the target azomethines was carried out by the interaction of aromatic aldehydes with 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide in an ethanol. The reaction was monitored by thin-layer chromatography (TLC). The determination of related impurities was done by HPLC. The analysis was carried out under the conditions of isocratic elution with a mobile phase of acetonitrile – water (70:30).Results and discussion. The results of the prediction of the biological activity of the constructed structures suggest the manifestation of cytostatic, antitubercular and anti-inflammatory activity characteristic of all target azomethines. The analysis of the reactivity revealed the influence of substituents of aldehydes contained in the aromatic core on the completeness of the condensation reaction. The spectral characteristics clearly confirmed the structure of the products, and the HPLC results showed the purity of the obtained substances, which is more than 95 %.Conclusion. As a result of the conducted studies, the structure of promising azomethine derivatives of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide was justified and the method of their synthesis and analysis by HPLC was optimized. In the future, the results of the research will allow us to identify the leading compounds with the specified pharmacological properties.

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17

Lobanov, P. S., A. L. Grebelkin, D. I. Zaitsev, V. A. Gindin, and A. A. Potekhin. "1,4,5,6-Tetrahydro-1,2,4-triazin-6-ones and 3-amino-1-imidazolin-4-ones from 2-aminoacylhydrazines." Chemistry of Heterocyclic Compounds 27, no. 10 (October 1991): 1116–19. http://dx.doi.org/10.1007/bf00486809.

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18

Krauze, A., Z. Andžāns, and G. Duburs. "Synthesis and Properties of Partially Hydrogenated Ethyl ([3,4']Bipyridin-6'-ylsulfanyl) Acetates." Latvian Journal of Chemistry 49, no. 1-4 (January 1, 2010): 66–71. http://dx.doi.org/10.2478/v10161-010-0002-z.

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Synthesis and Properties of Partially Hydrogenated Ethyl ([3,4']Bipyridin-6'-ylsulfanyl) Acetates Ethyl 2'-hydroxy-1',2',3',4'-tetrahydro[3,4']bipyridine-3'-carboxylate 3 and the corresponding ethyl 1',4'-dihydro[3,4']bipyridine-3'-carboxylate 4 as potential cardiovascular agents have been prepared by alkylation of 2'-hydroxy-1',2',3',4'-tetrahydro[3,4']bipyridine-6'-thiolate 1 or betaine 2 with ethyl bromoacetate. The treatment of [3,4']bipyridine 4 with KOH/H2O gave diethyl 3-amino-4-(pyridin-3-yl)-4,7-dihydrothieno[2,3-b]-pyridine-2,5-dicarboxylate 5, but subsequent treatment of the remaining reaction mixture with acetic acid excess gave ethyl 3-oxo-7-(pyridin-3-yl)-2,3-dihydro-7H-thiazolo[3,2-a]pyridine-6-carboxylate 7 - the product of intramolecular acylation. Compounds 4, 5 and 7 have been prepared using the one-pot synthesis method. Alkylation of [3,4']bipyridine 4 with iodomethane gave 1',4'-dihydro[3,4'] bipyridin-1-ium iodide 8.

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19

Mohamed, Shaaban K., Mehmet Akkurt, Muhammad N. Tahir, Antar A. Abdelhamid, and Mustafa R. Albayati. "2-Amino-4-(4-chlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile propan-2-one monosolvate." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 31, 2012): o1965—o1966. http://dx.doi.org/10.1107/s1600536812024142.

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In the title compound, C18H17ClN2O2·C3H6O, the 4H-pyran ring is nearly planar [maximum deviation = −0.108 (1) Å] and the cyclohexene ring is puckered [puckering parameters Q T = 0.4596 (17) Å, θ = 55.9 (2)° and φ = 226.5 (3)°]. The 4H-pyran ring is approximately perpendicular to the benzene ring [dihedral angle = 84.35 (7)°] and is almost coplanar with the mean plane of the cyclohexene ring [dihedral angle = 8.64 (7)°]. In the crystal, inversion-related main molecules are linked into dimers by pairs of N—H...N hydrogen bonds, generating an R 2 2(12) graph-set motif. These dimers are further connected by N—H...O and C—H...N hydrogen bonds, forming a layer structure extending parallel to the (011) plane. In addition, the molecules within the layers interact with each other via C—H...π interactions.

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20

Geffken, Detlef, and Maria Anna Köllner. "Cyclisierung von N′,N′-disubstituierten Anthranilsäurehydraziden mit 1,1′-Oxalyldiimidazol zu 4-Amino-2,3,4,5-tetrahydro-1H-1,4-benzodiaz- epin-2,3,5-trionen / Cyclization of N’,N’-Disubstituted Anthranilic Hydrazides with 1,1’-Oxalyldiimidazole to 4-Amino-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2,3,5-triones." Zeitschrift für Naturforschung B 60, no. 11 (November 1, 2005): 1207–11. http://dx.doi.org/10.1515/znb-2005-1115.

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N’,N’-Disubstituted (2-phenylamino)-, (2-methylamino)- and (2-benzylamino)benzohydrazides (1) are cyclized by in situ prepared 1,1’-oxalyldiimidazole to give 3-amino-2,3,4,5-tetrahydro-1H- 1,4-benzodiazepine-2,3,5-triones 2 as the major product. Depending on the substituents of 1 competitive formation of quinazoline-2,4-diones 3 and 1,3,4-oxadiazoline-2-one 4 is observed. The formation of heterocycles 2, 3, 4 is rationalized via a common primary intermediate 1A.

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21

Meany, Fiach B., Sarah O’Rourke, and Paul V. Murphy. "1-Tosyl-6-vinyl-4,5,6,7-tetrahydro-1H-benzo [d] imidazole-2-amine." Molbank 2021, no. 3 (July 31, 2021): M1262. http://dx.doi.org/10.3390/m1262.

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The alkene functionalised 2-aminobenzimidazole ring found in terrazoanthine natural products was synthesized in 3 steps from 1,2-epoxy-4-vinylcyclohexane via epoxide ring opening with toluenesulphonamide yielding 2 regioisomeric, separable amino alcohols. One isomer was oxidized to the corresponding ketone and subsequently condensed with cyanamide to furnish the title compound, which was characterized by 1H-NMR and 13C-NMR spectroscopy.

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22

Demchenko, S. A., Yu A. Fedchenkova, T. А. Bukhtiarova, L. S. Bobkova, V. V. Sukhoveev, and А. М. Demchenko. "Synthesis and anticancer activity of 1-(41-isopropylphenyl)-4-(42-chlorophenyl)5,6,7,8-tetrahydro-2,4а-diazacyclopenta[cd]azulene-2-carboxylic acid arylamides against PC-3 prostate cancer cells." Pharmacology and Drug Toxicology 13, no. 5 (December 25, 2019): 331–37. http://dx.doi.org/10.33250/vol13iss5pp331-337.

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Pharmacotherapy of prostate cancer is an important part in combating oncologic diseases. This is very relevant, because prostate cancer is a cause of 10 % of deaths from all cancerous diseases in males. The aim of the study – to synthesize novel derivatives of 1-(41-isopropylphenyl)-4-(42-chlorophenyl)5,6,7,8-tetrahydro-2,4а-diazacyclopenta[cd]azulene-2-carboxylic acid arylamides and to evaluate their antitumor activity against PC-3 prostate cancer cells. By reaction of equimolar amounts of 2-methoxy-3,4,5,6-tetrahydro-7H-azepine with a-amino-4-chloroacetophenone chlorohydrate, 3-(4-chlorophenyl)-6,7,8,9- tetrahydro-5Н-imidazo[1,2-a]azepine was synthesized. By alkylation of a-bromo-4-іsopropylacetophenone in ethylacetate and following treatment of the obtained intermediary quaternary salt with excess of 5 % NaOH solution,1-(41-isopropylphenyl)-4-(42chlorophenyl)-5,6,7,8-tetrahydro-2,4а-diazacyclopenta[cd] azulene was synthesized. By boiling it with equimolar amounts of correspondding arylisocyanates in dried benzol, an array of 1-(41-iso propylphenyl)-4(42-chlorophenyl)-5,6,7,8-tetrahydro-2,4а-diazacyclopenta[cd]azulene-2-carboxylic acid arylamides were synthesized. Structure and purity of all compounds obtained were confirmed by data of MR1Н spectroscopy. Lipophilicity (LogP) of compounds 6 and 8 a-i was calculated with the ACD LogP program. Antitumor activity of 1-(41-isopropylphenyl)-4-(42-chlorophenyl)-5,6,7,8-tetrahydro-2,4а-diazacyclopenta[cd]azulene-2-carboxylic acid (3-methylphenyl) and (3-methoxyphenyl)-amides was evaluated at in vitro test on prostate cancer PC-3 cell lines. It is indicated, that at concentration of 10–5 M these compounds exceed 5-fluorouracil as comparison drug in inhibiting PC-3 prostate cancer cells growth by 52.32 % and 3.93 % correspondingly. The data obtained substantiate feasibility of further studies of 1-(41-isopro pylphenyl)-4-(42-chlorophenyl)-5,6,7,8-tetrahydro-2,4а-diazacyclopenta[cd] azulene-2-carboxylic acid arylamides as new, potential antitumor medicines for prostate cancer treatment.

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23

El Ashry, El Sayed H., Laila Fathy Awad, and Omayma Kh Bdeewy. "Synthesis of tetrahydroindazol-4(5H)one and 7-thione from reaction of functionalized cyclic enaminones with hydrazine." Mediterranean Journal of Chemistry 7, no. 6 (January 9, 2019): 463–71. http://dx.doi.org/10.13171/mjc761901713eshea.

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Functionalized enaminones; 3-N-(aryl)amino-1--oxo-cyclohex-2-ene-2-dithiocarboxylates cyclohex-2-en-1-ones and 3-N-(aryl)amino-2-(N-aryl)thioamido-cyclohex-2-en-1-ones were obtained upon reaction of 3-N(aryl)amino-5,5-dimethyl-1-oxo-cyclohex-2-enes with carbon disulfide in presence of sodium hydroxide in DMSO, followed by methylation with dimethyl sulfate or with phenyl and p-bromophenyl isothiocyanates in toluene or under solvent-free condition, respectively. The cyclization of the dithioesters or the thioamides with hydrazine hydrate was accompanied by a displacement of the 3-N- arylamine moiety by a hydrazine group to give 6-hydrazino-4,4-dimethyl-1,3,4,5-tetrahydroindazole-7-thione or 3-N-(aryl)amino-4,5,6,7-tetrahydro-1H-indazole-4(5H)one respectively. Structure of the indazole derivatives formed was further confirmed from their reaction with acetone or p-nitrobenzaldehyde. The new structures were confirmed using 1HNMR, 13CNMR, 2DNMR, DEPT experiments and mass spectra.

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24

Gayathri, D., D. Velmurugan, G. Shanthi, P. T. Perumal, and K. Ravikumar. "4′-Amino-2,2′′-dioxo-2,2′′,3,3′′-tetrahydro-1H-indole-3-spiro-1′-cyclopent-3′-ene-2′-spiro-3′′-1H-indole-3′,5′,5′-tricarbonitrile dihydrate." Acta Crystallographica Section E Structure Reports Online 64, no. 2 (January 23, 2008): o501—o502. http://dx.doi.org/10.1107/s1600536808002146.

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25

Metwally, Mohamed Abbas, and Hassan Ali Etman. "The Synthesis of Indeno[l,2:4,5]pyrimido[l,2-a]benzimidazole-13-ones, Indeno[l,2-b]pyrazolo[4,3-e]pyridine-3,5-dione and Related Compounds*." Zeitschrift für Naturforschung B 41, no. 4 (April 1, 1986): 486–88. http://dx.doi.org/10.1515/znb-1986-0413.

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2-A rylidene-l,3-indaniones (1a and 2b ) reacts with 2-aminobenzimidazole in absolute ethanol, to yield 12,12a-dihydro-12-aryl-13H̱-indeno[1̄,2̄̄̄:4,5]pyrim ido[1,2-a̱]benzimidazole-13-one (2a and 2b). Treatm ent of 2a with PPA gave 15aH̱ -dibenzo[2̄,3̄:4̄,5̄]pentaleno[1̄,6̄:4,5,6]pyrimido- [1,2-a̱]benzimidazole (5). While the condensation of 1c with 3-amino-1-phenyl-2-pyrazolin-5-one in benzene in the presence of PTSA afforded 4-(2-hydroxyphenyl)-2,3a,4,4a-tetrahydro-2-phenylindeno[ 1,2-ḇ]pyrazolo[4,3-e̱]pyridine-3,5-dione (6a). However, the condensation of la with 2-amino-4,6-dihydroxypyrimidine gave the dimeric structure 7. The structures of the hitherto unknown ring systems have been confirmed by PMR, IR and mass spectral data

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26

Barton, Richard J., Keith E. Johnson, Beverly E. Robertson, F. Wayne Yerhoff, and Shengzhi Hu. "Structures of the pyrazolones formed by oxidative coupling of phenols with 4-aminoantipyrine." Canadian Journal of Chemistry 65, no. 9 (September 1, 1987): 2082–88. http://dx.doi.org/10.1139/v87-345.

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The structures of reaction products between 4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one and o-cresol, p-cresol, and p-ethylphenol are reported. The reaction of the former compound with phenols is used to estimate the concentration of phenol in potable water supplies. The reaction products are 2,3-dimethyl-4-[4-oxo-2,5-cyclohexadien-1-ylidene)amino]-1-phenyl-3-pyrazolin-5-one (monoclinic, P21/c, red, Z = 4, a = 7.092(1), b = 26.616(2), c = 8.644(2) Å, β = 79.17(3)°, 1432 reflections, R = 0.083, Rw = 0.040), 1,9a-dihydro-1,6,9a-trimethyl-2-phenylpyrazolo[3,4-b][1,4]benzoxazin-3(2H)-one (orthorhombic, Pbca, yellow, Z = 8, a = 18.943(3), b = 12.749(5), c = 13.223(2) Å, 2122 reflections, R = 0.067, Rw = 0.038), and 6-ethyl-1,9a-dihydro-1,9a-dimethyl-2-phenylpyrazolo[3,4-b|[1,4]benzoxazin-3(2H)-one (orthorhombic, Pbca, yellow, a = 18.895(11), b = 12.737(5), c = 14.041(6) Å, Z = 8, 1126 reflections, R = 0.068, Rw = 0.061), respectively. The latter two compounds rearrange to form 1,2,4,10-tetrahydro-1,6-dimethyl-2-phenyl-3H-pyrazolo[3,4-c][1,5]benzoxazepin-3-one (monoclinic, P21/c, white, Z = 8, a = 15.072(4), b = 14.491(4), c = 15.505(3) Å, β = 111.15(1)°, 3416 reflections, R = 0.101, Rw = 0.046) and 6-ethyl-1,2,4,10-tetrahydro-1-methyl-2-phenyl-3H-pyrazolo[3,4-c][1,5]benzoxazepin-3-one (monoclinic, C2/c, white, Z = 8, a = 33.768(3), b = 6.678(1), c = 15.836(2) Å, β = 115.41(1), 2805 reflections, R = 0.076, Rw = 0.043), respectively. The rearrangement is consistent with the observation that the pyrazolone rings of benzoxazinones are strained, as manifested by enlarged perimeters.

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27

Dharmalingam, V., A. K. Ramasamy, and V. Balasuramanian. "Synthesis and EPR Studies of Copper Metal Complexes of Dyes Derived from Remazol Red B, Procino Yellow, Fast Green FCF, Brilliant Cresyl Blue with Copper Acetate Monohydrate." E-Journal of Chemistry 8, s1 (2011): S211—S224. http://dx.doi.org/10.1155/2011/625365.

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The synthesis and characterization of four new solid dye complexes, CuL2(L= 2-[2-methoxy-5-(propane-1-sulfonyl)-phenyl azo]-naphthalen-1-ol, 5-{[3-(4,6-dihydroxy-[1,3,5]tri azine-2-ylamino)-phenyl]-hydrazones}-1-ethyl-4-methyl-2,6-dioxo-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid diethylamide, 4-{bis-[4-(benzyl-ethyl-amino)-phenyl]-methyl}-phenol and 7-imino-4-methyl-7H-phenoxazine-1,3-diamine) is reported. The mode for ligand coordination has been determined by IR and EPR spectra. The carboxyl and amino group of dyes coordinates to the Cu(II) atom as a unidentate or as a chelating ligand.

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LOBANOV, P. S., A. L. GREBELKIN, D. I. ZAITSEV, V. A. GINDIN, and A. A. POTEKHIN. "ChemInform Abstract: 1,4,5,6-Tetrahydro-1,2,4-triazin-6-ones and 3-Amino-1-imidazolin-4- ones from 2-Aminoacylhydrazines." ChemInform 24, no. 15 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199315103.

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29

Fareed, Ghulam, Mahboob A. Kalhoro, Muhammad A. Versiani, Nighat Afza, and Nazia Fareed. "7-{[2-(4-Hydroxyphenyl)methylidene]amino}-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid." Molbank 2012, no. 2 (May 10, 2012): M756. http://dx.doi.org/10.3390/m756.

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Li, Jing, and Ya-Wen Qiu. "Crystal structure of 2-amino-4-(3,4,5-trimethoxy-phenyl)-5-(oxo-5,6,7,8-tetrahydro-4H-chromene)-3-carbonitrile – ethanol (1/1), C21H26N2O6." Zeitschrift für Kristallographie - New Crystal Structures 232, no. 3 (May 24, 2017): 351–52. http://dx.doi.org/10.1515/ncrs-2016-0257.

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AbstractC21H26N2O6, triclinic P1̅ (no. 2), a = 8.1553(5) Å, b = 9.0739(9) Å, c = 14.6857(14) Å, α = 100.648(8)°, β = 102.355(7)°, γ = 90.450(6)°, V = 1042.03(16) Å3, Z = 2, Rgt(F) = 0.0538, wRref(F2) = 0.1533, T = 293(2) K.

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31

Mohamed, Hany M., Ashraf H. F. Abd EL-Wahab, Ahmed M. EL-Agrody, Ahmed H. Bedair, Fathy A. Eid, Mostafa M. Khafagy, and Kamal A. Abd-EL-Rehem. "Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities." Beilstein Journal of Organic Chemistry 7 (December 19, 2011): 1688–96. http://dx.doi.org/10.3762/bjoc.7.199.

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A series of 6,8-diiodocoumarin-3-N-carboxamides (4–11) were prepared. Treatment of ethyl 6,8-diiodocoumarin-3-carboxylate (1) with ethyl cyanoacetate/NH4OAc gave ethyl 2-(3-carbamoyl-6,8-diiodocoumarin-4-yl)-2-cyanoacetate (12) and 2-amino-4-hydroxy-7,9-diiodocoumarino[3,4-c]pyridine-1-carbonitrile (13), and treatment with acetone in the presence of NH4OAc or methylamine gave the ethyl 4-oxo-2,6-methano-2-methyl-3,4,5,6-tetrahydro-8,10-diiodobenzo[2,1-g]-2H-1,3-oxazocine-5-carboxylate derivatives 14a,b. All compounds were evaluated for their antimicrobial activity and the compounds 12–14a,b exhibited a pronounced effect on all tested microorganisms.

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32

Wang, Xiang-Shan, Jian-Rong Wu, Qing Li, and Shu-Jiang Tu. "A Green Method for the Synthesis of Novel benzo[b]pyran Derivatives in an Ionic Liquid." Journal of Chemical Research 2009, no. 4 (April 2009): 234–36. http://dx.doi.org/10.3184/030823409x431373.

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A series of novel 2-amino-5,6,7,8-tetrahydro-4,7,7-trimethyl-5-oxo-4-aryl-4 H-benzo[ b]pyran-3-carbonitriles was obtained from the reaction of 2-(1-arylethylidene)malononitrile and 5,5-dimethylcyclohexane-1,3-dione in an ionic liquid at 90°C. This method had the advantages of operational simplicity, mild reaction conditions and an environmentally benign procedure.

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33

Rahman Badal, Md Mizanur, Md Tarikul Islam, Reshma Parvin, Md Abul Khaer Morol, Md Maniruzzaman, Mohammad Abu Yousuf, and Md Ershad Halim. "Antimicrobial, Structure-Activity Relationship and Computational Studies of Some Synthesized Chalcone Derivatives." Asian Journal of Chemistry 33, no. 3 (2021): 644–50. http://dx.doi.org/10.14233/ajchem.2021.23028.

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Several chalcones viz. 1,3-diaryl-2-propane-1-one (1a), 3-(4-hydroxy phenyl)-1-phenyl-2-propane-1- one (1b), 3-(4-amino-phenyl)-1-phenyl-2-propane-1-one (1c) and their derivatives 2-ethoxy-4,6- diphenyl-4H-pyran-3-carboxylic acid ethyl ester (2a), 4-(4-hydroxy-phenyl)-7,7-dimethyl-2-phenyl- 4,6,7,8-tetrahydro-chromen-5-one (2b) and 7-(4-amino-phenyl)-5-phenyl-1,5-dihydropyrano[2,3- d]pyrimidine-2,4-dione (2c ) have been synthesized following both conventional and microwave irradiation methods. The structures of the isolated compounds were elucidated on the basis of UV-visible, FTIR, 1H NMR spectral data. The antimicrobial results showed some remarkable facts about the structure–activity relationship, which states that the electronic atmosphere around the chalcone derivative moieties and substituents considerably affect the antimicrobial potential of the synthesized compounds. Theoretical calculation as well as antimicrobial activity of the compounds were also studied.

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34

Zhang, Guang-Hui. "Crystal structure of 2-amino-4-(3,4-difluorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H12N2O2F2." Zeitschrift für Kristallographie - New Crystal Structures 231, no. 1 (March 1, 2016): 223–24. http://dx.doi.org/10.1515/ncrs-2015-0097.

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Shi, Daqing, Jie Mou, Qiya Zhuang, and Xiangshan Wang. "One-pot synthesis of 2-amino-4-aryl-5-oxo-5,6,7,8-tetrahydro-4H-1-benzopyran-3-carbonitriles in aqueous media." Journal of Chemical Research 2004, no. 12 (December 1, 2004): 821–23. http://dx.doi.org/10.3184/0308234043431294.

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36

Ashalatha, B. V., B. Narayana, K. K. Vijaya Raj, and N. Suchetha Kumari. "Synthesis of some new bioactive 3-amino-2-mercapto-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one derivatives." European Journal of Medicinal Chemistry 42, no. 5 (May 2007): 719–28. http://dx.doi.org/10.1016/j.ejmech.2006.11.007.

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37

Makki, Mohammed S. I., Reda M. Abdel-Rahman, and Khalid A. Khan. "Fluorine Substituted 1,2,4-Triazinones as Potential Anti-HIV-1 and CDK2 Inhibitors." Journal of Chemistry 2014 (2014): 1–14. http://dx.doi.org/10.1155/2014/430573.

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Fluorine substituted 1,2,4-triazinones have been synthesized via alkylation, amination, and/or oxidation of 6-(2-amino-5-fluorophenyl)-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one1and 4-fluoro-N-(4-fluoro-2-(5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-6-yl)phenyl)benzamide5as possible anti-HIV-1 and CDK2 inhibitors. Alkylation on positions 2 and 4 in 1,2,4-triazinone gave compounds6–8. Further modification was performed by selective alkylation and amination on position 3 to form compounds9–15. However oxidation of5yielded compounds16–18. Structures of the target compounds have been established by spectral analysis data. Five compounds (5, 11, 14, 16, and17) have shown very good anti-HIV activity in MT-4 cells. Similarly, five compounds (1, 3, and14–16) have exhibited very significant CDK2 inhibition activity. Compounds14and16were found to have dual anti-HIV and anticancer activities.

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Mahmoud, M. R., A. A. Shalaby, T. A. Gad, and A. A. El-Khamry. "A facile synthesis and heteroannulation of pyrido[2,3-d]pyrimidine and related heterocyclic systems." Journal of Chemical Research 2009, no. 10 (October 2009): 612–15. http://dx.doi.org/10.3184/030823409x12523324765777.

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7-Amino-1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-(3,4,5-trimethoxyphenyl)pyrido[2,3- d]pyrimidine (1) was prepared and reacted with methyl iodide and ethyl chloroacetate to give the S-alkylated products 2 and 3, respectively. The reaction of 1 or 3 with hydrazine hydrate yielded the same 2-hydrazino derivative 4. Treatment of 4 with 2,4-pentanedione, 2-acetylcyclohexanone and ethyl acetoacetate afforded the corresponding pyrazolylpyrido[2,3- d]pyrimidine derivatives (5–7), while phthalic anhydride gave the phthalazinyl compound 8. Ethoxymethylenemalononitrile with the hydrazine 4 formed the fused 1,2,4-triazepine 9, while triazolopyrido[2,3- d]pyrimidines were obtained from the reaction of 4 with benzylidene malononitrile or benzaldehyde (forming 10), acetic acid/anhydride (giving 11), and ethyl chloroformate (giving 12).

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Behm, Helmut, Paul T. Beurskens, Ralf Plate, and Harry C. J. Ottenheijm. "Crystal structure determination of 1-[N-benzyloxycarbonyl-1-amino-(S-4-methoxybenzyl)-2-thio-ethyl] -2-hydroxy-3-ethoxycarbonyl-1,2,3,4 -tetrahydro-β-carboline, C32 H35 N3 O6 S." Recueil des Travaux Chimiques des Pays-Bas 105, no. 7-8 (1986): 238–40. http://dx.doi.org/10.1002/recl.19861050711.

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Yoshitake, Ikufumi, and Kazuhiro Kubo. "Effects of l-[(2-Thiazolin-2-yl)amino]acetyl-4-(l,3-dithiol-2-ylidene)-2,3,4,5-tetrahydro-1H-1-benzazepin-3,5-dione Hydrochloride (KF-14363) on Active Oxygen Production." Japanese Journal of Pharmacology 57, no. 2 (1991): 137–45. http://dx.doi.org/10.1254/jjp.57.137.

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41

Sharma, Bhavik,, and Sushil Kumar Agarwal. "RP-HPLC Method Development and Validation for Estimation of Acebrophylline." Asian Journal of Pharmaceutical Research and Development 6, no. 6 (February 14, 2019): 56–59. http://dx.doi.org/10.22270/ajprd.v6i6.446.

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Acebrophylline is an anti-inflammatory and airway mucus regulator. It had ambroxol and theophylline-7-acetic acid, the former facilitates the biosynthesis of pulmonary surfactant which raises blood levels of ambroxol, by stimulating surfactant production. Chemical structure of acebrophylline is 1, 2, 3, 6- tetrahydro-1, 3-dimethyl-2, 6-dioxo-7H-purine-7-aceticacidwithtrans-4-[(2-amino-3, 5 dibromophenyl) methyl] aminio] cyclohexanol. Survey revealed that various analytical methods like spectrophotometric, HPLC, and RP-HPLC, have been reported for the determination of Ambroxol HCl and Theophylline-7-acetic acid, individually and in combination with some other drugs. The aim of present study was to develop and validate stability indicating HPLC method for the analyses of acebrophylline. High performance liquid chromatographic method has been developed for the estimation of Acebrophylline. Reported methods also include RP-HPLC method for determination of Acebrophylline. The developed UV spectrophotometric method is simple and requires less time for the analysis. It is also rapid and economic method.

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42

Parekh, H. P., M. H. Chauhan, N. L. Solanki, and V. H. Shah. "A Clean, Benign, Energy Efficient One-Pot Multicomponent Synthesis and Bio-evaluation of Novel [1,2,4]Triazolo[1,5-a]quinolines." Asian Journal of Organic & Medicinal Chemistry 6, no. 2 (2021): 111–15. http://dx.doi.org/10.14233/ajomc.2021.ajomc-p322.

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In present work, a series of novel [1,2,4]triazolo[1,5-a]quinoline derivatives (HP-101-110) have been synthesized using multi-component reaction at room temperature in the presence of ammonium chloride as mild, cost effective green catalyst along with water as eco-friendly green solvent. The synthesis of 1,2,4-triazolo[1,5-a]quinolines (HP-101-110) was achieved by two step process. In first step, diversified Hantzsch pyridine reaction of an appropriate aromatic aldehyde, malononitrile, dimedone and benz hydrazide using ethanol as a solvent gives N-(2-amino-3-cyano-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8- tetrahydro-quinolin-1(4H)-yl)-4-hydroxybenzamide derivatives. In the second step, synthesis of the final product 2-(4-hydroxyphenyl)-8,8-dimethyl-6-oxo-5-phenyl-6,7,8,9-tetrahydro[1,2,4]triazolo[1,5- a]-quinoline-4-carbonitriles was achieved by the intramolecular cyclization of step 1 product.The structure of all the synthesized compounds (HP101-110) has been elucidated by FT-IR, 1H & 13C NMR, mass spectral data and elemental analyses.

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Dyachenko, I. V., E. B. Rusanov, A. V. Gutov, and M. V. Vovk. "Synthesis and alkylation of 1-alkyl(aryl)-4-cyano-3-dicyanomethylene-substituted carbo[c]fused pyridines. Molecular and crystal structure of 2-(4-cyano-1-methyl-5,6,7,8-tetrahydroisoquinolin-3-yl)-2-(2-oxo-2-phenylethyl)malononitrile and 10-amino-8-phenyl-5-(2-chlorophenyl)-1,2,3,4-tetrahydro-7H-pyrido[2′,3′:3,4]cyclopenta[1,2-c]isoquinoline-7,7,9-tricarbonitrile." Russian Journal of General Chemistry 83, no. 7 (July 2013): 1383–93. http://dx.doi.org/10.1134/s1070363213070141.

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Guerrero, Sergio A., Juan E. Ramírez, Alirio Palma, Justo Cobo, and Christopher Glidewell. "A concise and versatile route to tetrahydro-1-benzazepines carrying [a]-fused heterocyclic units: synthetic sequence and spectroscopic characterization, and the molecular and supramolecular structures of one intermediate and two products." Acta Crystallographica Section C Structural Chemistry 75, no. 2 (January 25, 2019): 168–77. http://dx.doi.org/10.1107/s2053229619000871.

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A concise, efficient and versatile route from simple starting materials to tricyclic tetrahydro-1-benzazepines carrying [a]-fused heterocyclic units is reported. Thus, the easily accessible methyl 2-[(2-allyl-4-chlorophenyl)amino]acetate, (I), was converted, via (2RS,4SR)-7-chloro-2,3,4,5-tetrahydro-1,4-epoxy-1-benzo[b]azepine-2-carboxylate, (II), to the key intermediate methyl (2RS,4SR)-7-chloro-4-hydroxy-2,3,4,5-tetrahydro-1H-benzo[b]azepine-2-carboxylate, (III). Chloroacetylation of (III) provided the two regioisomers methyl (2RS,4SR)-7-chloro-1-(2-chloroacetyl)-4-hydroxy-2,3,4,5-tetrahydro-1H-benzo[b]azepine-2-carboxylate, (IVa), and methyl (2RS,4SR)-7-chloro-4-(2-chloroacetoxy)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-2-carboxylate, C14H15Cl2NO4, (IVb), as the major and minor products, respectively, and further reaction of (IVa) with aminoethanol gave the tricyclic target compound (4aRS,6SR)-9-chloro-6-hydroxy-3-(2-hydroxyethyl)-2,3,4a,5,6,7-hexahydrobenzo[f]pyrazino[1,2-a]azepine-1,4-dione, C15H17ClN2O4, (V). Reaction of ester (III) with hydrazine hydrate gave the corresponding carbohydrazide (VI), which, with trimethoxymethane, gave a second tricyclic target product, (4aRS,6SR)-9-chloro-6-hydroxy-4a,5,6,7-tetrahydrobenzo[f][1,2,4]triazino[4,5-a]azepin-4(3H)-one, C12H12ClN3O2, (VII). Full spectroscopic characterization (IR, 1H and 13C NMR, and mass spectrometry) is reported for each of compounds (I)–(III), (IVa), (IVb) and (V)–(VII), along with the molecular and supramolecular structures of (IVb), (V) and (VII). In each of (IVb), (V) and (VII), the azepine ring adopts a chair conformation and the six-membered heterocyclic rings in (V) and (VII) adopt approximate boat forms. The molecules in (IVb), (V) and (VII) are linked, in each case, into complex hydrogen-bonded sheets, but these sheets all contain a different range of hydrogen-bond types: N—H...O, C—H...O, C—H...N and C—H...π(arene) in (IVb), multiple C—H...O hydrogen bonds in (V), and N—H...N, O—H...O, C—H...N, C—H...O and C—H...π(arene) in (VII).

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Jeffery, D., D. M. Rutherford, P. D. J. Weitzman, and G. G. Lunt. "Purification and partial characterization of 4-aminobutyrate:2-oxoglutarate aminotransferase from sheep brain and locust ganglia." Biochemical Journal 249, no. 3 (February 1, 1988): 795–99. http://dx.doi.org/10.1042/bj2490795.

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We report here the first purification to homogeneity of 4-aminobutyrate: 2-oxoglutarate aminotransferase (EC 2.6.1.19) (GABA-T) from an invertebrate source (locust) and its initial comparison with that of GABA-T from mammalian brain (sheep). The enzyme from both organisms was found to be a dimer of similar-sized subunits, with a native Mr of approx. 97,000. The pI of GABA-T from the locust was 6.7 and that of the sheep enzyme was 5.5. Michaelis constants for 4-aminobutyric acid (GABA) and 2-oxoglutarate were respectively 0.79 +/- 0.16 mM and 0.27 +/- 0.08 mM for the locust enzyme and 2.2 +/- 0.24 mM and 0.22 +/- 0.11 mM for the sheep enzyme. 5-(Aminomethyl)-3-isoxazolol (muscimol) was a competitive inhibitor of both enzymes, whereas 5-amino-1,3-cyclohexadienylcarboxylic acid (gabaculine) acted as a potent suicide substrate. However, 3-aminopropane-1-sulphonic acid, diaminobutyric acid, 1,2,3,4-tetrahydro-1-methyl-3-pyridinecarboxylic acid (isoguvacine), beta-(aminomethyl)-4-chlorobenzenepropanoic acid (baclofen), bicuculline and picrotoxin did not inhibit either enzyme at concentrations below 100 mM. Polyclonal antisera raised against GABA-T from the sheep failed to cross-react with the enzyme from locust in either an Ouchterlony immunodiffusion plate or a competitive enzyme-linked immunosorbent assay. The purification procedures differed considerably. Ion-exchange chromatography, which was found suitable for the purification of GABA-T from the sheep, was ineffective with locust enzyme, which was finally purified by hydrophobic-interaction chromatography and chromatofocusing.

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Aghekyan, A. A., G. G. Mkryan, H. A. Panosyan, G. M. Buniatyan, and R. E. Muradyan. "Synthesis and Antioxidant Activity of Ethyl 2-Amino-6-cyano-6-phenyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylates and 3-Amino-4-oxo-7-phenyl-3,4,5,6,7,8-hexahydrobenzo[4,5]thieno[2,3-d]pyrimidine-7-carbonitriles." Russian Journal of Organic Chemistry 56, no. 3 (March 2020): 440–45. http://dx.doi.org/10.1134/s1070428020030124.

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47

Erichsen, Mette N., Tri H. V. Huynh, Bjarke Abrahamsen, Jesper F. Bastlund, Christoffer Bundgaard, Olja Monrad, Anders Bekker-Jensen, et al. "Structure−Activity Relationship Study of First Selective Inhibitor of Excitatory Amino Acid Transporter Subtype 1: 2-Amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (UCPH-101)." Journal of Medicinal Chemistry 53, no. 19 (October 14, 2010): 7180–91. http://dx.doi.org/10.1021/jm1009154.

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48

El-mahdy, Kamelia, Azza El-Kazak, Mohamed Abdel-Megid, Magdy Seada, and Osama Farouk. "Synthesis, Characterization and Biological Evaluation of some New Thieno[2,3-d]Pyrimidine Derivatives." JOURNAL OF ADVANCES IN CHEMISTRY 5, no. 1 (April 29, 2009): 581–91. http://dx.doi.org/10.24297/jac.v5i1.937.

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Abstract:

10-Oxo-4,6,7,8,9,10-hexahydroprazolo[1,5-a][1]benzothieno[2,3-d]pyrimidine-3-carbaldehyde (2) was prepared by Vilsmeier-Haack reaction of 3-amino-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one (1). Reaction of carbaldehyde derivative 2 with malononitrile afforded arylidene malononitrile 3. Cyclization of the latter compound with thiourea yielded pyrimidinethione 4. Interaction of carbaldehyde derivative 2 in presence of thiourea with keto- compounds such as ethyl acetoacetate, or acetylacetone, or dimedone or ethyl cyanoacetate gave pyrimidine derivatives 5-8. Hydrazinolysis of carbaldehyde derivative 2 gave the hydrazone 9. Reaction of the latter with phenyl isothiocyanate afforded thiosemicarbazone 10, which underwent cyclization with oxalyl chloride to give thioxoimidazolidinedione 11. Condensation of compound 2 with thiosemicarbazide furnished thiosemicarbazone derivative 12. Reaction of compound 2 with aminopyrazolone in the presence of an acid and/or a base afforded pyrazolones 13 and 14. Treatment of carbaldehyde derivative 2 with cyanoacetohydrazide gave acrylohydrazide 15. Interaction of the latter with carbon disulfide yielded mercaptooxadiazole 16. Condensation of compound 2 with acetylpyridazinone 17 produced chalcone 18. Reaction of compound 18 with malononitrile in pyridine gave cyanopyran 19, while its reaction with malononitrile in presence of ammonium acetate in ethanol yielded cyanopyridine 20. Structures of the newly synthesized products have been deduced on the basis of elemental analysis and spectral data. The synthesized compounds were screened for their antimicrobial activity.

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Santagati, Andrea, Maria Santagati, and Maria Modica. "Synthesis of 2,3,5,6,7,8-Hexahydro-3-amino-2-thioxo[1]benzothieno[2,3-d]pyrimidin-4(1H)-one and Derivatives of the New Heterocyclic System 7,8,9,10-Tetrahydro-3H,11H-[1]benzothieno[2',3':4,5]pyrimido[2,1-b][1,3,4]thiadiazin-11-one." HETEROCYCLES 36, no. 6 (1993): 1315. http://dx.doi.org/10.3987/com-92-6304.

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Yang, Zhipei, Kai Zhang, Fangbin Gong, Shayu Li, Jun Chen, Jin Shi Ma, Lyubov N. Sobenina, Albina I. Mikhaleva, Guoqiang Yang, and Boris A. Trofimov. "A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative." Beilstein Journal of Organic Chemistry 7 (January 12, 2011): 46–52. http://dx.doi.org/10.3762/bjoc.7.8.

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Abstract:

Molecules containing polarized NH fragments that behave as anion-binding motifs are widely used as receptors for recognition and sensing purposes in aprotic solvents. We present here a new example of a receptor, 3-amino-5-(4,5,6,7-tetrahydro-1H-indol-2-yl)isoxazole-4-carboxamide (receptor 1), which contains pyrrole, amide and amino subunits. This receptor shows both changes in its UV–vis absorption and fluorescence emission spectra upon the addition of F−, resulting in highly selectivity for fluoride detection over other anions, such as Cl−, Br−, I−, HSO4 −, H2PO4 − and AcO− in CH3CN. 1H NMR titration, time-dependent density functional theory (TDDFT) calculations and other experiments confirm that the sensing process is brought about by deprotonation of the pyrrole-NH in receptor 1.

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