Details der Publikation - Synthesis, computational study and cytotoxicity of 4-hydroxycoumarin-derived imines/enamines

Synthesis, computational study and cytotoxicity of 4-hydroxycoumarin-derived imines/enamines

Abstract In this study, we applied a direct condensation between 3-acetyl-4-hydroxy-2H-chromen-2-one and different amines (anilines and benzyl amines) in order to synthesize some coumarin-based imines/enamines (3a–o) as cytotoxic agents. All the compounds were characterized by means of FT-IR, NMR, mass spectroscopy and elemental analyses. Since the title compounds can exist as different forms including (s-cis)-imine and (s-trans)-imine or (E and Z)-enamines, their conformational and geometrical aspects were investigated computationally by DFT method. The optimized geometry parameters, ΔE, ΔG, ΔH, Mulliken atomic charge, HOMO and LUMO energy, and NBO analysis suggested that these compounds can exist predominantly in (E)-enamine form. All the synthesized compounds (3a–o) were evaluated in vitro for their cytotoxic activities against cancer cell lines (MCF-7 and A549) and normal cell line (BEAS-2B) using the MTT assay. The 4-hydroxybenzyl derivative 3k was found to be the most potent cytotoxic agent with no selectivity, similar to doxorubicin. However, the 4-chlorobenzyl analog 3o could be considered as an equipotent compound respect to doxorubicin with higher selectivity. Graphic abstract.

Medienart:	E-Artikel

Erscheinungsjahr:	2020
Erschienen:	2020

Enthalten in:	Zur Gesamtaufnahme - volume:25
Enthalten in:	Molecular diversity - 25(2020), 2 vom: 22. Apr., Seite 1011-1024

Sprache:	Englisch

Beteiligte Personen:	Vaseghi, Samaneh [VerfasserIn] Yousefi, Mohammad [VerfasserIn] Shokrzadeh, Mohammad [VerfasserIn] Hossaini, Zinatossadat [VerfasserIn] Hosseini-khah, Zahra [VerfasserIn] Emami, Saeed [VerfasserIn]

Links:	Volltext [lizenzpflichtig]

BKL:	42.00$jBiologie: Allgemeines
Themen:	-chromen-2-one 2 Anticancer Computational study Coumarin DFT Schiff bases

Anmerkungen:	© Springer Nature Switzerland AG 2020

doi:	10.1007/s11030-020-10086-2

funding:
Förderinstitution / Projekttitel:

PPN (Katalog-ID):	OLC2125550172

Internformat


LEADER	01000naa a22002652 4500
001	OLC2125550172
003	DE-627
005	20230505103505.0
007	cr uuu---uuuuu
008	230505s2020 xx \|\|\|\|\|o 00\| \|\|eng c
024	7		\|a 10.1007/s11030-020-10086-2 \|2 doi
035			\|a (DE-627)OLC2125550172
035			\|a (DE-He213)s11030-020-10086-2-e
040			\|a DE-627 \|b ger \|c DE-627 \|e rakwb
041			\|a eng
082	0	4	\|a 570 \|q VZ
084			\|a 42.00$jBiologie: Allgemeines \|2 bkl
100	1		\|a Vaseghi, Samaneh \|e verfasserin \|4 aut
245	1	0	\|a Synthesis, computational study and cytotoxicity of 4-hydroxycoumarin-derived imines/enamines
264		1	\|c 2020
336			\|a Text \|b txt \|2 rdacontent
337			\|a Computermedien \|b c \|2 rdamedia
338			\|a Online-Ressource \|b cr \|2 rdacarrier
500			\|a © Springer Nature Switzerland AG 2020
520			\|a Abstract In this study, we applied a direct condensation between 3-acetyl-4-hydroxy-2H-chromen-2-one and different amines (anilines and benzyl amines) in order to synthesize some coumarin-based imines/enamines (3a–o) as cytotoxic agents. All the compounds were characterized by means of FT-IR, NMR, mass spectroscopy and elemental analyses. Since the title compounds can exist as different forms including (s-cis)-imine and (s-trans)-imine or (E and Z)-enamines, their conformational and geometrical aspects were investigated computationally by DFT method. The optimized geometry parameters, ΔE, ΔG, ΔH, Mulliken atomic charge, HOMO and LUMO energy, and NBO analysis suggested that these compounds can exist predominantly in (E)-enamine form. All the synthesized compounds (3a–o) were evaluated in vitro for their cytotoxic activities against cancer cell lines (MCF-7 and A549) and normal cell line (BEAS-2B) using the MTT assay. The 4-hydroxybenzyl derivative 3k was found to be the most potent cytotoxic agent with no selectivity, similar to doxorubicin. However, the 4-chlorobenzyl analog 3o could be considered as an equipotent compound respect to doxorubicin with higher selectivity. Graphic abstract
650		4	\|a Anticancer
650		4	\|a 2
650		4	\|a -chromen-2-one
650		4	\|a Coumarin
650		4	\|a Schiff bases
650		4	\|a Computational study
650		4	\|a DFT
700	1		\|a Yousefi, Mohammad \|4 aut
700	1		\|a Shokrzadeh, Mohammad \|4 aut
700	1		\|a Hossaini, Zinatossadat \|4 aut
700	1		\|a Hosseini-khah, Zahra \|4 aut
700	1		\|a Emami, Saeed \|4 aut
773	0	8	\|i Enthalten in \|t Molecular diversity \|d Springer International Publishing, 1995 \|g 25(2020), 2 vom: 22. Apr., Seite 1011-1024 \|h Online-Ressource \|w (DE-627)311010377 \|w (DE-600)2003589-5 \|w (DE-576)121190846 \|x 1573-501X \|7 nnns
773	1	8	\|g volume:25 \|g year:2020 \|g number:2 \|g day:22 \|g month:04 \|g pages:1011-1024
856	4	0	\|u https://dx.doi.org/10.1007/s11030-020-10086-2 \|z lizenzpflichtig \|3 Volltext
912			\|a GBV_USEFLAG_A
912			\|a SYSFLAG_A
912			\|a GBV_OLC
912			\|a GBV_ILN_11
912			\|a GBV_ILN_20
912			\|a GBV_ILN_22
912			\|a GBV_ILN_23
912			\|a GBV_ILN_24
912			\|a GBV_ILN_31
912			\|a GBV_ILN_32
912			\|a GBV_ILN_39
912			\|a GBV_ILN_40
912			\|a GBV_ILN_60
912			\|a GBV_ILN_62
912			\|a GBV_ILN_63
912			\|a GBV_ILN_69
912			\|a GBV_ILN_70
912			\|a GBV_ILN_73
912			\|a GBV_ILN_74
912			\|a GBV_ILN_90
912			\|a GBV_ILN_95
912			\|a GBV_ILN_100
912			\|a GBV_ILN_101
912			\|a GBV_ILN_105
912			\|a GBV_ILN_110
912			\|a GBV_ILN_120
912			\|a GBV_ILN_138
912			\|a GBV_ILN_150
912			\|a GBV_ILN_151
912			\|a GBV_ILN_152
912			\|a GBV_ILN_161
912			\|a GBV_ILN_170
912			\|a GBV_ILN_171
912			\|a GBV_ILN_187
912			\|a GBV_ILN_213
912			\|a GBV_ILN_224
912			\|a GBV_ILN_230
912			\|a GBV_ILN_250
912			\|a GBV_ILN_281
912			\|a GBV_ILN_285
912			\|a GBV_ILN_293
912			\|a GBV_ILN_370
912			\|a GBV_ILN_602
912			\|a GBV_ILN_636
912			\|a GBV_ILN_702
912			\|a GBV_ILN_2001
912			\|a GBV_ILN_2003
912			\|a GBV_ILN_2004
912			\|a GBV_ILN_2005
912			\|a GBV_ILN_2006
912			\|a GBV_ILN_2007
912			\|a GBV_ILN_2008
912			\|a GBV_ILN_2009
912			\|a GBV_ILN_2010
912			\|a GBV_ILN_2011
912			\|a GBV_ILN_2014
912			\|a GBV_ILN_2015
912			\|a GBV_ILN_2020
912			\|a GBV_ILN_2021
912			\|a GBV_ILN_2025
912			\|a GBV_ILN_2026
912			\|a GBV_ILN_2027
912			\|a GBV_ILN_2031
912			\|a GBV_ILN_2034
912			\|a GBV_ILN_2037
912			\|a GBV_ILN_2038
912			\|a GBV_ILN_2039
912			\|a GBV_ILN_2044
912			\|a GBV_ILN_2048
912			\|a GBV_ILN_2049
912			\|a GBV_ILN_2055
912			\|a GBV_ILN_2057
912			\|a GBV_ILN_2059
912			\|a GBV_ILN_2061
912			\|a GBV_ILN_2064
912			\|a GBV_ILN_2065
912			\|a GBV_ILN_2068
912			\|a GBV_ILN_2088
912			\|a GBV_ILN_2093
912			\|a GBV_ILN_2106
912			\|a GBV_ILN_2107
912			\|a GBV_ILN_2108
912			\|a GBV_ILN_2110
912			\|a GBV_ILN_2111
912			\|a GBV_ILN_2112
912			\|a GBV_ILN_2113
912			\|a GBV_ILN_2118
912			\|a GBV_ILN_2129
912			\|a GBV_ILN_2132
912			\|a GBV_ILN_2143
912			\|a GBV_ILN_2144
912			\|a GBV_ILN_2147
912			\|a GBV_ILN_2148
912			\|a GBV_ILN_2152
912			\|a GBV_ILN_2153
912			\|a GBV_ILN_2188
912			\|a GBV_ILN_2190
912			\|a GBV_ILN_2232
912			\|a GBV_ILN_2336
912			\|a GBV_ILN_2446
912			\|a GBV_ILN_2470
912			\|a GBV_ILN_2474
912			\|a GBV_ILN_2507
912			\|a GBV_ILN_2522
912			\|a GBV_ILN_2548
912			\|a GBV_ILN_4035
912			\|a GBV_ILN_4037
912			\|a GBV_ILN_4046
912			\|a GBV_ILN_4112
912			\|a GBV_ILN_4125
912			\|a GBV_ILN_4126
912			\|a GBV_ILN_4242
912			\|a GBV_ILN_4246
912			\|a GBV_ILN_4249
912			\|a GBV_ILN_4251
912			\|a GBV_ILN_4305
912			\|a GBV_ILN_4306
912			\|a GBV_ILN_4307
912			\|a GBV_ILN_4313
912			\|a GBV_ILN_4322
912			\|a GBV_ILN_4323
912			\|a GBV_ILN_4324
912			\|a GBV_ILN_4325
912			\|a GBV_ILN_4326
912			\|a GBV_ILN_4328
912			\|a GBV_ILN_4333
912			\|a GBV_ILN_4334
912			\|a GBV_ILN_4335
912			\|a GBV_ILN_4336
912			\|a GBV_ILN_4338
912			\|a GBV_ILN_4393
912			\|a GBV_ILN_4700
936	b	k	\|a 42.00$jBiologie: Allgemeines \|q VZ \|0 106419943 \|0 (DE-625)106419943
951			\|a AR
952			\|d 25 \|j 2020 \|e 2 \|b 22 \|c 04 \|h 1011-1024

Synthesis, computational study and cytotoxicity of 4-hydroxycoumarin-derived imines/enamines

Zugang & Verfügbarkeit

Zugehörige Publikationen/Bände