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Open AccessShort Note

2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid

by Sangeetha Karanth, Badiadka Narayana, Sharath Chandra Kodandoor and Balladka Kunhanna Sarojini

Molbank 2018, 2018(3), M1009; https://doi.org/10.3390/M1009 - 29 Jul 2018

Cited by 1 | Viewed by 3339

Thia-Michael addition of 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazine-1-carbothioamide (1) with maleic anhydride results in the formation of the title compound 2-{[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl acetic acid 2. The precursor 1 is synthesized by the reaction of 4-hydroxy-3,5-dimethoxybenzaldehyde and thiosemicarbazide in the presence of glacial acetic acid as [...] Read more.

Thia-Michael addition of 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazine-1-carbothioamide (1) with maleic anhydride results in the formation of the title compound 2-{[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl acetic acid 2. The precursor 1 is synthesized by the reaction of 4-hydroxy-3,5-dimethoxybenzaldehyde and thiosemicarbazide in the presence of glacial acetic acid as the catalyst. The structure of the title compound is determined by elemental analysis, FT-IR, ¹H-NMR, ¹³C-NMR and mass spectral data. In order to determine the molecular interactions with the bacterial enzyme, the title compound is further docked into the active site of the MurB protein of Staphylococcus aureus (PDB ID: 1HSK). The in vitro antibacterial and antifungal activity of the title compound is carried out in order to appraise its antimicrobial efficacy by determination of zone of inhibition and minimal inhibitory concentration. The compound is also evaluated for its antioxidant property by 2,2-diphenyl-1-picryl-hydrazyl (DPPH) radical scavenging assay. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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6 pages, 1998 KB

Open AccessShort Note

1-[5-(4-Ethoxyphenyl)-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one

by Sangeetha Karanth, Badiadka Narayana, Jayashree Avvadukkam and Balladka Kunhanna Sarojini

Molbank 2018, 2018(2), M1000; https://doi.org/10.3390/M1000 - 19 Jun 2018

Viewed by 2921

Abstract

The cyclization reaction of 3-(4-ethoxyphenyl)-1-(naphthalen-1-yl)prop-2-en-1-one (1) using hydrazine hydrate in acetic acid medium culminates, resulting in the title compound 1-[5-(4-ethoxyphenyl)-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one (2). The structure of the newly synthesized compound is determined by IR, ¹H-NMR, ¹³C-NMR and [...] Read more.

The cyclization reaction of 3-(4-ethoxyphenyl)-1-(naphthalen-1-yl)prop-2-en-1-one (1) using hydrazine hydrate in acetic acid medium culminates, resulting in the title compound 1-[5-(4-ethoxyphenyl)-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one (2). The structure of the newly synthesized compound is determined by IR, ¹H-NMR, ¹³C-NMR and mass spectral data. In order to evaluate the putative molecular interactions, the title compound (2) is docked against the active site of Cytochrome P₄₅₀ 14α-sterol demethylase (CYP51) from Mycobacterium tuberculosis. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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9 pages, 2260 KB

Open AccessShort Note

(Z)-4-[2-(3,4-Difluorophenyl)hydrazono]-3-methyl-1H-pyrazol-5(4H)-one

by Billava Jayappa Mohan, Balladka Kunhanna Sarojini, Badiadka Narayana and Enumadishetty Srinivasulu Sindhu Priya

Molbank 2018, 2018(2), M989; https://doi.org/10.3390/M989 - 31 Mar 2018

Cited by 2 | Viewed by 4587

Abstract

The title compound (Z)-4-[2-(3,4-difluorophenyl)hydrazono]-3-methyl-1H-pyrazol-5(4H)-one 4 was synthesized by the reaction of ethyl 2-[2-(3,4-difluorophenyl)hydrazono]-3-oxobutanoate 3 with hydrazine hydrate. The diazotization of 3,4-difluoroaniline, followed by the treatment with ethyl acetoacetate, afforded intermediate 3. The synthesized compound 4 was [...] Read more.

The title compound (Z)-4-[2-(3,4-difluorophenyl)hydrazono]-3-methyl-1H-pyrazol-5(4H)-one 4 was synthesized by the reaction of ethyl 2-[2-(3,4-difluorophenyl)hydrazono]-3-oxobutanoate 3 with hydrazine hydrate. The diazotization of 3,4-difluoroaniline, followed by the treatment with ethyl acetoacetate, afforded intermediate 3. The synthesized compound 4 was characterized by FTIR, ¹H-NMR, ¹³C-NMR and LCMS, and it showed synergistic anti-inflammatory, antiproliferative and antibacterial activities. Full article

(This article belongs to the Special Issue Heterocycles)

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4 pages, 467 KB

Open AccessShort Note

N-(4-Nitrophenyl)-2-{2-[3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl]-4-oxo-4,5-dihydro-1,3-thiazol-5-yl}acetamide

by Vinutha V. Salian, Badiadka Narayana and Balladka K. Sarojini

Molbank 2017, 2017(2), M943; https://doi.org/10.3390/M943 - 10 Jun 2017

Cited by 4 | Viewed by 3805

Abstract

In the present investigation, the synthesis and spectroscopic characterization of N-(4-nitrophenyl)-2-{2-[3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl]-4-oxo-4,5-dihydro-1,3-thiazol-5-yl}acetamide (2) is performed. The title compound (2) is synthesized by the reaction of 3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5- dihydro-1H-pyrazole-1-carbothioamide (1) with N-(4-nitrophenyl)maleimide. The cyclization of title compound is evidenced by FT-IR, NMR, and LCMS data. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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5 pages, 89 KB

Open AccessShort Note

2'-[(4-Fluorophenyl)carbonyl]-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indole-3,3'-pyrrolizin]-2(1H)-one

by Majal Sapnakumari, Badiadka Narayana, Seranthimata Samshuddin and Balladka Kunhanna Sarojini

Molbank 2013, 2013(2), M802; https://doi.org/10.3390/M802 - 23 May 2013

Cited by 2 | Viewed by 3973

Abstract

A new spiro[indole-3,3'-pyrrolizine] derivative is regioselectively synthesized by the straightforward multicomponent reaction of 1-(4-fluorophenyl)-3-phenylprop-2-en-1-one, isatin and L-proline without any catalyst. The structure of the newly synthesized compound is characterized by IR, NMR, UV-visible and mass spectral data. The compound is also screened for [...] Read more.

A new spiro[indole-3,3'-pyrrolizine] derivative is regioselectively synthesized by the straightforward multicomponent reaction of 1-(4-fluorophenyl)-3-phenylprop-2-en-1-one, isatin and L-proline without any catalyst. The structure of the newly synthesized compound is characterized by IR, NMR, UV-visible and mass spectral data. The compound is also screened for its reducing power assay. Full article

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4 pages, 68 KB

Open AccessShort Note

2-{[5-(Diphenylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}-N-(pyrazin-2-yl)acetamide

by Prakash S. Nayak, Badiadka Narayana, Seranthimata Samshuddin and Balladka Kunhanna Sarojini

Molbank 2013, 2013(2), M800; https://doi.org/10.3390/M800 - 3 May 2013

Cited by 1 | Viewed by 5522

Abstract

S-Alkylation of 5-(diphenylmethyl)-1,3,4-oxadiazole-2(3H)-thione (3) by 2-chloro-N-(pyrazin-2-yl)acetamide (2) affords the title compound, 2-{[5-(diphenylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}-N-(pyrazin-2-yl)acetamide (4). The intermediate (2), in turn, was prepared by the acetylation of 2-aminopyrazine (1) [...] Read more.

S-Alkylation of 5-(diphenylmethyl)-1,3,4-oxadiazole-2(3H)-thione (3) by 2-chloro-N-(pyrazin-2-yl)acetamide (2) affords the title compound, 2-{[5-(diphenylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}-N-(pyrazin-2-yl)acetamide (4). The intermediate (2), in turn, was prepared by the acetylation of 2-aminopyrazine (1) with chloroacetyl chloride. The structure of the newly synthesized compound is characterized by IR, NMR and mass spectral data. Full article

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11 pages, 821 KB

Open AccessArticle

Synthesis and Crystal Structures of N-Substituted Pyrazolines

by Wan-Sin Loh, Ching Kheng Quah, Tze Shyang Chia, Hoong-Kun Fun, Majal Sapnakumari, Badiadka Narayana and Balladka Kunhanna Sarojini

Molecules 2013, 18(2), 2386-2396; https://doi.org/10.3390/molecules18022386 - 20 Feb 2013

Cited by 11 | Viewed by 7403

Abstract

Four pyrazole compounds, 3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbaldehyde (1), 5-(4-bromophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde (2), 1-[5-(4-chlorophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone (3) and 1-[3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]propan-1-one (4), have been prepared by condensing chalcones with hydrazine hydrate in the presence of aliphatic acids, [...] Read more.

Four pyrazole compounds, 3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbaldehyde (1), 5-(4-bromophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde (2), 1-[5-(4-chlorophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone (3) and 1-[3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]propan-1-one (4), have been prepared by condensing chalcones with hydrazine hydrate in the presence of aliphatic acids, namely formic acid, acetic acid and propionic acid. The structures were characterized by X-ray single crystal structure determination. The dihedral angles formed between the pyrazole and the fluoro-substituted rings are 4.64(7)° in 1, 5.3(4)° in 2 and 4.89(6)° in 3. In 4, the corresponding angles for molecules A and molecules B are 10.53(10)° and 9.78(10)°, respectively. Full article

(This article belongs to the Section Organic Chemistry)

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4 pages, 165 KB

Open AccessShort Note

2-(4-Fluoro-3-nitrophenyl)-6-(4-methoxyphenyl)imidazo[2,1-b]-1,3,4-thiadiazole

by Umesha Kundapur, Balladka Kunhanna Sarojini and Badiadka Narayana

Molbank 2012, 2012(4), M778; https://doi.org/10.3390/M778 - 25 Sep 2012

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Abstract

The title compound, 2-(4-fluoro-3-nitrophenyl)-6-(4-methoxyphenyl)imidazo[2,1-b]-1,3,4-thiadiazole (3) was obtained by the condensation of 5-(4-fluoro-3-nitrophenyl)-[1,3,4]thiadiazol-2-ylamine (1) with 4-methoxyphenacyl bromide (2). The newly prepared imidazo[2,1-b]-1,3,4-thiadiazole derivative (3) was characterized by IR, ¹H-NMR, ¹³C-NMR and LCMS spectral data. Full article

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9 pages, 316 KB

Open AccessArticle

Crystal and Molecular Structure Studies of Ethyl 4-(4-Hydroxyphenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate and Ethyl 4-(3-Bromophenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate

by Manpreet Kaur, Jerry P. Jasinski, Ray J. Butcher, Hemmige S. Yathirajan, Anil N. Mayekar and Badiadka Narayana

Crystals 2012, 2(3), 1239-1247; https://doi.org/10.3390/cryst2031239 - 27 Aug 2012

Cited by 1 | Viewed by 7370

Abstract

The crystal and molecular structures of the title compounds, ethyl 4-(4-hydroxyphenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate (I) and ethyl 4-(3-bromophenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate (II), are reported and confirmed by single crystal X-ray diffraction data. Compound (I), C₂₆H₂₄O₅, crystallizes from [...] Read more.

The crystal and molecular structures of the title compounds, ethyl 4-(4-hydroxyphenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate (I) and ethyl 4-(3-bromophenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate (II), are reported and confirmed by single crystal X-ray diffraction data. Compound (I), C₂₆H₂₄O₅, crystallizes from a methanol solution in the monoclinic C2/c space group with eight molecules in the unit cell. The unit cell parameters are: a = 25.4114(5) Å, b = 8.47440(10) Å, c = 20.6921(4) Å, β = 108.328(2)° and V = 4229.92(13) Å³. Disorder is observed throughout the entire molecule with an occupancy ratio 0.690(2):0.310(2). Compound (II), C₂₆H₂₃O₄Br, crystallizes from an ethyl acetate solution in the monoclinic P2₁/c spacegroup with four molecules in the unit cell. The unit cell parameters are a = 17.8991(9) Å, b = 11.4369(6) Å, c = 10.8507(5) Å, β = 92.428(4)° and V = 2219.25(19) Å³. Disorder is observed in the cyclohexenone ring and the carboxylate group with an occupancy ratio 0.830(6):0.170(6). Weak O–H...O (I) or C–H...O (II) intermolecular interactions are observed which influence crystal packing stability. These chalcone derivative types of molecules are important in their ability to act as activated unsaturated systems in conjugated addition reactions of carbanions in the presence of basic catalysts which exhibit a multitude of biological activities. Full article

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4 pages, 62 KB

Open AccessShort Note

4-[5-(3,5-Difluorophenyl)furan-2-yl]-2,3,7-triazaspiro[4.5]dec-3-en-1-one Hydrochloride

by Rajagopalan Srinivasan, Badiadka Narayana, Seranthimata Samshuddin and Balladka Kunhanna Sarojini

Molbank 2012, 2012(3), M773; https://doi.org/10.3390/M773 - 24 Aug 2012

Cited by 1 | Viewed by 4244

Abstract

A novel route for the synthesis of new spirocyclic derivative is developed. The present work involves the synthesis of title compound 3 by Suzuki coupling of 3,5-difluorophenyl boronic acid with tert-butyl 1-(5-bromofuran-2-yl)-4-oxo-2,3,7-triazaspiro[4.5]dec-1-ene-7-carboxylate (2), which in turn prepared from the ethyl [...] Read more.

A novel route for the synthesis of new spirocyclic derivative is developed. The present work involves the synthesis of title compound 3 by Suzuki coupling of 3,5-difluorophenyl boronic acid with tert-butyl 1-(5-bromofuran-2-yl)-4-oxo-2,3,7-triazaspiro[4.5]dec-1-ene-7-carboxylate (2), which in turn prepared from the ethyl nipecotate (1). Newly prepared spirocyclic derivative (3) is characterized by IR, NMR and mass spectral data. Full article

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4 pages, 70 KB

Open AccessShort Note

3-(4-Fluorophenyl)-N-[4-(4-furan-2-yl-1-oxo-2,3,7-triazaspiro[4.5]dec-3-en-2-yl)phenyl]propionamide Hydrochloride

by Rajagopalan Srinivasan, Badiadka Narayana, Seranthimata Samshuddin and Balladka Kunhanna Sarojini

Molbank 2012, 2012(3), M771; https://doi.org/10.3390/M771 - 17 Aug 2012

Cited by 1 | Viewed by 4624

Abstract

A simple and novel route for the synthesis of new spirocyclic propionamide derivative is developed. The present work involves N-arylation of pyrazolone (1) using copper(I) iodide catalyst followed by reduction to give amine (2). The coupling of 2 [...] Read more.

A simple and novel route for the synthesis of new spirocyclic propionamide derivative is developed. The present work involves N-arylation of pyrazolone (1) using copper(I) iodide catalyst followed by reduction to give amine (2). The coupling of 2 with 3-(4-fluorophenyl)propionic acid and deprotection of Boc group yields the title compound (3). Full article

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8 pages, 273 KB

Open AccessArticle

Synthesis, Characterization and Crystal Structures of 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide and 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide

by Jerry P. Jasinski, James A. Golen, Seranthimata Samshuddin, Badiadka Narayana and Hemmige S. Yathirajan

Crystals 2012, 2(3), 1108-1115; https://doi.org/10.3390/cryst2031108 - 15 Aug 2012

Cited by 13 | Viewed by 7588

Abstract

Two new pyrazoline derivatives, 3,5-bis(4-fluorophenyl)-4,5-dihydropyrazole-1-carboxamide (1) and 3,5-bis(4-fluorophenyl)-4,5-dihydropyrazole-1-carbothioamide (2), were synthesized by reacting 4,4'-difluoro chalcone with semicarbazide hydrochloride and thiosemicarbazide in ethanolic sodium hydroxide solution. Both the compounds were confirmed by single crystal X-ray diffraction data and supported by [...] Read more.

Two new pyrazoline derivatives, 3,5-bis(4-fluorophenyl)-4,5-dihydropyrazole-1-carboxamide (1) and 3,5-bis(4-fluorophenyl)-4,5-dihydropyrazole-1-carbothioamide (2), were synthesized by reacting 4,4'-difluoro chalcone with semicarbazide hydrochloride and thiosemicarbazide in ethanolic sodium hydroxide solution. Both the compounds were confirmed by single crystal X-ray diffraction data and supported by IR, NMR, and mass spectral data. In 1, crystal packing is stabilized by N–H…O hydrogen bonds and weak N–H...N, N–H…F and C–H…F intermolecular interactions. In 2, only weak N–H…F and N–H…S intermolecular interactions are observed. Crystal data: C₁₆H₁₃F₂N₃O, (1), M_r= 301.29, monoclinic, C2/c, a = 17.6219(6) Å, b = 10.8735(3) Å, c = 15.3216(5) Å, β = 102.864(3)°, V = 2862.11(16) Å³, Z = 8, T = 173 K, R(F) = 0.0511, wR(F²) = 0.1333; C₁₆H₁₃F₂N₃S, (2), M_r= 317.35, monoclinic, P2₁/c, a = 14.339(2) Å, b = 11.1478(17) Å, c = 9.541(2)(5) Å, β = 107.007(18)°, V = 1458.5(5) Å³, Z = 4, T = 173 K, R(F) = 0.0413, wR(F²) = 0.0959. Full article

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4 pages, 66 KB

Open AccessShort Note

N-(3,4-Dimethoxyphenyl)-4-oxo-2,3,7-triazaspiro[4.5]dec-1-ene-1-carboxamide Hydrochloride

by Rajagopalan Srinivasan, Badiadka Narayana, Seranthimata Samshuddin and Balladka Kunhanna Sarojini

Molbank 2012, 2012(3), M769; https://doi.org/10.3390/M769 - 8 Aug 2012

Cited by 3 | Viewed by 3839

Abstract

A simple and novel route for synthesis of new spirocyclic amide derivative is developed. The present work involves the oxidative cleavage of tert-butyl 1-(furan-2-yl)-4-oxo-2,3,7-triazaspiro[4.5]dec-1-ene-7-carboxylate 1 followed by the amine coupling and deprotection of Boc. Full article

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4 pages, 86 KB

Open AccessShort Note

(2E)-3-[4-(1H-Benzimidazol-2-ylmethoxy)-3-methoxyphenyl]-1-(4,4''-difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl)prop-2-en-1-one

by Seranthimata Samshuddin, Badiadka Narayana, Divya N. Shetty, Rajagopalan Srinivasan and Balladka Kunhanna Sarojini

Molbank 2012, 2012(3), M764; https://doi.org/10.3390/M764 - 4 Jul 2012

Cited by 3 | Viewed by 4644

Abstract

Novel terphenyl chalcone containing benzimidazole moiety (3) is synthesized by the base-catalyzed Claisen–Schmidt condensation of acetyl terphenyl derivative (1) with 4-(1H-benzimidazol-2-ylmethoxy)-3-methoxybenzaldehyde (2). Newly prepared chalcone derivative (3) is characterized by IR, NMR and mass spectral data. Full article

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4 pages, 110 KB

Open AccessShort Note

tert-Butyl 1-(Furan-2-yl)-4-oxo-2,3,7-triazaspiro[4.5]dec-1-ene-7-carboxylate

by Rajagopalan Srinivasan, Badiadka Narayana, Seranthimata Samshuddin and Balladka Kunhanna Sarojini

Molbank 2012, 2012(2), M757; https://doi.org/10.3390/M757 - 24 May 2012

Cited by 3 | Viewed by 4294

Abstract

A simple and novel route for synthesis of new spirocyclic compound is developed. The present work involves condensation of ethyl nipecotate with 2-furaldehyde followed by the MnO₂ oxidation to give the β-keto ester which upon reaction with hydrazine hydrate gives the [...] Read more.

A simple and novel route for synthesis of new spirocyclic compound is developed. The present work involves condensation of ethyl nipecotate with 2-furaldehyde followed by the MnO₂ oxidation to give the β-keto ester which upon reaction with hydrazine hydrate gives the spiro pyrazolone. Full article

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