Biologically Active 1-Arylpiperazines. Synthesis of New N-(4-Aryl-1-piperazinyl)alkyl Derivatives of Quinazolidin-4(3H)-one, 2,3-Dihydrophthalazine-1,4-dione and 1,2-Dihydropyridazine-3,6-dione as Potential Serotonin Receptor Ligands

Kowalski, Piotr; Kowalska, Teresa; Mokrosz, Maria J.; Bojarski, Andrzej J.; Charakchieva-Minol, Sijka

doi:10.3390/60900784

Cited by 16 publications

(9 citation statements)

References 23 publications

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“…Benzoxazolinone was recently employed in the synthesis of new arylpiperazine derivatives which produced pharmacological results when systematic modifications were made in the amide part of this molecule. With respect to the importance of the mentioned pharmacophore group property of benzoxazolinone, phosphorus ylide 4 involving a 2‐benzoxazolinone was chosen to investigate the dynamic 1 H NMR effects. The experimental data of 1 H, 13 C and 31 P NMR indicated the two rotational isomers of ylide 4 with the major 4‐( Z ) and minor 4‐( E ) forms .…”

Section: Introductionmentioning

confidence: 97%

Dynamic ¹H NMR investigation along with a theoretical study around the C–C and C = C bonds in a particular phosphorus ylide

Habibi‐Khorassani

Maghsoodlou

Ebrahimi

et al. 2012

J of Physical Organic Chem

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In the present work, the dynamic 1 H NMR effects were investigated at variable temperatures within a particular phosphorus ylide involving a 2-benzoxazolinone around the carbon-carbon single bond and also partial carbon-carbon double bond in two Zand E-rotational isomers. Activation and kinetic parameters including ΔH 6 ¼ , ΔG 6 ¼ , ΔS 6 ¼ and E a were determined in accord with the dynamic 1 H NMR data for three rotational processes. In addition, theoretical studies based upon rotation around the same bonds were investigated using ab initio and DFT methods at the HF/6-31G(d,p) and B3LYP/6-31G(d,p) levels of theory. Theoretical activation and kinetic parameters including ΔH 6 ¼ , ΔG 6 ¼ , ΔS 6 ¼ and E a were calculated at 298 K and experimental temperatures for five rotational processes. These results (experimental and theoretical), taken together, indicate that the rotational energy barrier around the C = C double bond was considerably high and the observation of the two rotational isomers was impossible (seen as a single isomer) at the high temperatures, in this case rotation around the C = C bond was too fast on the NMR time scale. When the temperature was relatively low, the rate of rotation was sufficiently slow; therefore, observation of the two Zand E-isomers was possible. In addition, calculations at the HF/6-31G(d,p) level of theory showed very favorable results in agreement with the experimental data on rotation around the C = C bond. While, B3LYP level using the 6-31G(d,p) basis set was provided the reasonable data for the restricted rotations around the C-C and C-N single bond.

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Section: Introductionmentioning

confidence: 97%

Dynamic ¹H NMR investigation along with a theoretical study around the C–C and C = C bonds in a particular phosphorus ylide

Habibi‐Khorassani

Maghsoodlou

Ebrahimi

et al. 2012

J of Physical Organic Chem

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“…Antiprotozoal acivity, in particular towards trichomonas and amoebas is shown by Nsubstituted derivatives of imidazole containing nitro group in 2-or 5-position. This work is a continuation of our research on synthesis of azaheterocyclic compounds and studies of their bioactivity [8][9][10][11]. Metronidazole is an antibacterial and antiprotozoal drug, which also has a radiosensitising effect on hypoxic tumor cells.…”

Section: Introductionmentioning

confidence: 97%

Synthesis and Prediction of Bioactivity of New Nitroimidazole Derivatives.

2005

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“…Piperazinyl amide fragments have the ability to form several hydrogen bonds, modulate the acid-base equilibrium constant and change the octanol-water partition coefficient [13]. They are considered as the basic motif for designing many biologically active molecules [14,15]. Some piperazinyl amides of 18βglycyrrhetinic acid (c) are synthesized using various methods.…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid

Cai

Zhang

Meng

et al. 2020

Beilstein J. Org. Chem.

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In the present study, a practical method to prepare piperazinyl amides of 18β-glycyrrhetinic acid was developed. Two main procedures for the construction of important intermediate 8 are discussed. One procedure involves the amidation of 1-Boc-piperazine with 3-acetyl-18β-glycyrrhetinic acid, prepared by the reaction of 18β-glycyrrhetinic acid with acetic anhydride without any solvent at 130 °C. The other procedure to prepare compound 8 involves the amidation of 18β-glycyrrhetinic acid followed by the esterification with acetic anhydride. Finally, compound 8 underwent N-Boc deprotection to prepare product 4. To ascertain the scope of the reaction, another C-3 ester derivative 17 was tested under the optimized reaction conditions. Furthermore, the reasons for the appearance of byproducts were elucidated. Crystallographic data of a selected piperazinyl amide is reported.

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Biologically Active 1-Arylpiperazines. Synthesis of New N-(4-Aryl-1-piperazinyl)alkyl Derivatives of Quinazolidin-4(3H)-one, 2,3-Dihydrophthalazine-1,4-dione and 1,2-Dihydropyridazine-3,6-dione as Potential Serotonin Receptor Ligands

Abstract: The synthesis of a series of new n-propyl and n-butyl chain containing 1-aryl-piperazine derivatives of quinazolidin-4(3H)-one (7) 2-phenyl-2,3-dihydrophthalazine-1,4-dione (8) and 1-phenyl-1,2-dihydropyridazine-3,6-dione (9) as potential serotonin receptor ligands is described.

Cited by 16 publications

References 23 publications

Dynamic ¹H NMR investigation along with a theoretical study around the C–C and C = C bonds in a particular phosphorus ylide

Dynamic ¹H NMR investigation along with a theoretical study around the C–C and C = C bonds in a particular phosphorus ylide

Synthesis and Prediction of Bioactivity of New Nitroimidazole Derivatives.

Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid

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Biologically Active 1-Arylpiperazines. Synthesis of New N-(4-Aryl-1-piperazinyl)alkyl Derivatives of Quinazolidin-4(3H)-one, 2,3-Dihydrophthalazine-1,4-dione and 1,2-Dihydropyridazine-3,6-dione as Potential Serotonin Receptor Ligands

Abstract: The synthesis of a series of new n-propyl and n-butyl chain containing 1-aryl-piperazine derivatives of quinazolidin-4(3H)-one (7) 2-phenyl-2,3-dihydrophthalazine-1,4-dione (8) and 1-phenyl-1,2-dihydropyridazine-3,6-dione (9) as potential serotonin receptor ligands is described.

Cited by 16 publications

References 23 publications

Dynamic 1H NMR investigation along with a theoretical study around the C–C and C = C bonds in a particular phosphorus ylide

Dynamic 1H NMR investigation along with a theoretical study around the C–C and C = C bonds in a particular phosphorus ylide

Synthesis and Prediction of Bioactivity of New Nitroimidazole Derivatives.

Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid

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Product

Resources

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Dynamic ¹H NMR investigation along with a theoretical study around the C–C and C = C bonds in a particular phosphorus ylide

Dynamic ¹H NMR investigation along with a theoretical study around the C–C and C = C bonds in a particular phosphorus ylide