2-[(2,6-Dimethylmorpholin-4-yl)methyl]-4-[(E)-2-{3- [(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4- hydroxy-5-methoxyphenyl}ethenyl]-1H-pyrazol-5- yl}ethenyl]-6-methoxyphenol

Joko Untung; Iskandarsyah Iskandarsyah; Hayun Hayun

doi:10.3390/M949

2-[(2,6-Dimethylmorpholin-4-yl)methyl]-4-[(E)-2-{3- [(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4- hydroxy-5-methoxyphenyl}ethenyl]-1H-pyrazol-5- yl}ethenyl]-6-methoxyphenol

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

A novel di-Mannich derivative of curcumin pyrazole, 2-[(2,6-dimethyl morpholin-4- yl)methyl]-4-[(E)-2-{3-[(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4-hydroxy-5-methoxyphenyl} ethenyl]-1H-pyrazol-5-yl}ethenyl]-6-methoxyphenol (2), has been synthesized through a Mannich reaction of curcumin pyrazole (1), formaldehyde, and 2,6-dimethylmorpholine. The structure of the synthesized compound was confirmed on the basis of FTIR, ¹H-NMR, ¹³C-NMR, 2D Heteronuclear Single-Quantum Correlation (HSQC) and 2D Heteronuclear Multiple Bond Correlation (HMBC), and mass spectral data. The water solubility was evaluated and the result showed that compound 2 was three times more soluble than that of curcumin pyrazole (1) and curcumin.

Original language	English
Article number	M949
Journal	MolBank
Volume	2017
Issue number	3
DOIs	https://doi.org/10.3390/M949
Publication status	Published - Sept 2017

Keywords

2,6-dimethylmorpholine
Curcumin pyrazole
Di-mannich derivative
Water solubility

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@article{40894ab8faa247cdbe474debc811e37e,

title = "2-[(2,6-Dimethylmorpholin-4-yl)methyl]-4-[(E)-2-\{3- [(E)-2-\{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4- hydroxy-5-methoxyphenyl\}ethenyl]-1H-pyrazol-5- yl\}ethenyl]-6-methoxyphenol",

abstract = "A novel di-Mannich derivative of curcumin pyrazole, 2-[(2,6-dimethyl morpholin-4- yl)methyl]-4-[(E)-2-\{3-[(E)-2-\{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4-hydroxy-5-methoxyphenyl\} ethenyl]-1H-pyrazol-5-yl\}ethenyl]-6-methoxyphenol (2), has been synthesized through a Mannich reaction of curcumin pyrazole (1), formaldehyde, and 2,6-dimethylmorpholine. The structure of the synthesized compound was confirmed on the basis of FTIR, 1H-NMR, 13C-NMR, 2D Heteronuclear Single-Quantum Correlation (HSQC) and 2D Heteronuclear Multiple Bond Correlation (HMBC), and mass spectral data. The water solubility was evaluated and the result showed that compound 2 was three times more soluble than that of curcumin pyrazole (1) and curcumin.",

keywords = "2,6-dimethylmorpholine, Curcumin pyrazole, Di-mannich derivative, Water solubility",

author = "Joko Untung and Iskandarsyah Iskandarsyah and Hayun Hayun",

note = "Funding Information: We thank the Directorate of Research and Community Services, Universitas Indonesia, Depok, Indonesia, for the financial support of this research. We are also thankful to the Research Center for Chemistry, the Indonesian Institute of Sciences, Serpong, Indonesia, and to the Chemistry Study Program, Faculty of Natural Sciences, Bandung Institute of Technology (ITB), Bandung, Indonesia, for recording spectral data. Publisher Copyright: {\textcopyright} 2017 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2017",

month = sep,

doi = "10.3390/M949",

language = "English",

volume = "2017",

journal = "MolBank",

issn = "1422-8599",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "3",

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TY - JOUR

T1 - 2-[(2,6-Dimethylmorpholin-4-yl)methyl]-4-[(E)-2-{3- [(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4- hydroxy-5-methoxyphenyl}ethenyl]-1H-pyrazol-5- yl}ethenyl]-6-methoxyphenol

AU - Untung, Joko

AU - Iskandarsyah, Iskandarsyah

AU - Hayun, Hayun

N1 - Funding Information: We thank the Directorate of Research and Community Services, Universitas Indonesia, Depok, Indonesia, for the financial support of this research. We are also thankful to the Research Center for Chemistry, the Indonesian Institute of Sciences, Serpong, Indonesia, and to the Chemistry Study Program, Faculty of Natural Sciences, Bandung Institute of Technology (ITB), Bandung, Indonesia, for recording spectral data. Publisher Copyright: © 2017 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2017/9

Y1 - 2017/9

N2 - A novel di-Mannich derivative of curcumin pyrazole, 2-[(2,6-dimethyl morpholin-4- yl)methyl]-4-[(E)-2-{3-[(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4-hydroxy-5-methoxyphenyl} ethenyl]-1H-pyrazol-5-yl}ethenyl]-6-methoxyphenol (2), has been synthesized through a Mannich reaction of curcumin pyrazole (1), formaldehyde, and 2,6-dimethylmorpholine. The structure of the synthesized compound was confirmed on the basis of FTIR, 1H-NMR, 13C-NMR, 2D Heteronuclear Single-Quantum Correlation (HSQC) and 2D Heteronuclear Multiple Bond Correlation (HMBC), and mass spectral data. The water solubility was evaluated and the result showed that compound 2 was three times more soluble than that of curcumin pyrazole (1) and curcumin.

AB - A novel di-Mannich derivative of curcumin pyrazole, 2-[(2,6-dimethyl morpholin-4- yl)methyl]-4-[(E)-2-{3-[(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4-hydroxy-5-methoxyphenyl} ethenyl]-1H-pyrazol-5-yl}ethenyl]-6-methoxyphenol (2), has been synthesized through a Mannich reaction of curcumin pyrazole (1), formaldehyde, and 2,6-dimethylmorpholine. The structure of the synthesized compound was confirmed on the basis of FTIR, 1H-NMR, 13C-NMR, 2D Heteronuclear Single-Quantum Correlation (HSQC) and 2D Heteronuclear Multiple Bond Correlation (HMBC), and mass spectral data. The water solubility was evaluated and the result showed that compound 2 was three times more soluble than that of curcumin pyrazole (1) and curcumin.

KW - 2,6-dimethylmorpholine

KW - Curcumin pyrazole

KW - Di-mannich derivative

KW - Water solubility

UR - https://www.scopus.com/pages/publications/85027057498

U2 - 10.3390/M949

DO - 10.3390/M949

M3 - Article

AN - SCOPUS:85027057498

SN - 1422-8599

VL - 2017

JO - MolBank

JF - MolBank

IS - 3

M1 - M949

ER -

2-[(2,6-Dimethylmorpholin-4-yl)methyl]-4-[(E)-2-{3- [(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4- hydroxy-5-methoxyphenyl}ethenyl]-1H-pyrazol-5- yl}ethenyl]-6-methoxyphenol

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