Details der Publikation - Synthesis and biological evaluation of ursolic acid derivatives containing an aminoguanidine moiety

Synthesis and biological evaluation of ursolic acid derivatives containing an aminoguanidine moiety

Abstract Three series of ursolic acid derivatives containing an aminoguanidine moiety were designed, synthesized, and evaluated for anti-bacterial and anti-inflammatory activity. Some compounds displayed potent anti-bacterial activity against Gram-positive bacterial strains (including multidrug-resistant clinical isolates) and Gram-negative bacterial strains, with minimum inhibitory concentration (MIC) values in the range of 2–64 µg/mL. Compounds 3a, 5a, and 7l showed significant inhibitory activity against the Gram-positive bacterial strain Staphylococcus aureus RN 4220, the Gram-negative bacterial strain Escherichia coli 1924, and four multidrug-resistant Gram-positive bacterial strains, with MIC values of 2 and 4 µg/mL. In anti-inflammatory tests, most of the compounds exhibited potent activity, in particular compound 3a displayed the most potent activity with 81.61% inhibition after intraperitoneal administration, which was more potent than ursolic acid and the reference drugs (ibuprofen and indomethacin). The cytotoxic activity of compound 3a was assessed in HeLa, Hep3B, and A549 cells..

Medienart:	E-Artikel

Erscheinungsjahr:	2019
Erschienen:	2019

Enthalten in:	Zur Gesamtaufnahme - volume:28
Enthalten in:	Medicinal chemistry research - 28(2019), 7 vom: 27. Apr., Seite 959-973

Sprache:	Englisch

Beteiligte Personen:	Wu, Jie [VerfasserIn] Ma, Song [VerfasserIn] Zhang, Tian-Yi [VerfasserIn] Wei, Zhi-Yu [VerfasserIn] Wang, Hui-Min [VerfasserIn] Guo, Fang-Yan [VerfasserIn] Zheng, Chang-Ji [VerfasserIn] Piao, Hu-Ri [VerfasserIn]

Links:	Volltext [lizenzpflichtig]

Themen:	Aminoguanidine Anti-inflammatory activity Antibacterial activity Cytotoxicity Ursolic acid

Anmerkungen:	© Springer Science+Business Media, LLC, part of Springer Nature 2019

doi:	10.1007/s00044-019-02349-x

funding:
Förderinstitution / Projekttitel:

PPN (Katalog-ID):	OLC2096116562

Internformat


LEADER	01000naa a22002652 4500
001	OLC2096116562
003	DE-627
005	20230331233043.0
007	cr uuu---uuuuu
008	230331s2019 xx \|\|\|\|\|o 00\| \|\|eng c
024	7		\|a 10.1007/s00044-019-02349-x \|2 doi
035			\|a (DE-627)OLC2096116562
035			\|a (DE-He213)s00044-019-02349-x-e
040			\|a DE-627 \|b ger \|c DE-627 \|e rakwb
041			\|a eng
082	0	4	\|a 540 \|a 610 \|q VZ
084			\|a PHARM \|q DE-84 \|2 fid
100	1		\|a Wu, Jie \|e verfasserin \|4 aut
245	1	0	\|a Synthesis and biological evaluation of ursolic acid derivatives containing an aminoguanidine moiety
264		1	\|c 2019
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 Science+Business Media, LLC, part of Springer Nature 2019
520			\|a Abstract Three series of ursolic acid derivatives containing an aminoguanidine moiety were designed, synthesized, and evaluated for anti-bacterial and anti-inflammatory activity. Some compounds displayed potent anti-bacterial activity against Gram-positive bacterial strains (including multidrug-resistant clinical isolates) and Gram-negative bacterial strains, with minimum inhibitory concentration (MIC) values in the range of 2–64 µg/mL. Compounds 3a, 5a, and 7l showed significant inhibitory activity against the Gram-positive bacterial strain Staphylococcus aureus RN 4220, the Gram-negative bacterial strain Escherichia coli 1924, and four multidrug-resistant Gram-positive bacterial strains, with MIC values of 2 and 4 µg/mL. In anti-inflammatory tests, most of the compounds exhibited potent activity, in particular compound 3a displayed the most potent activity with 81.61% inhibition after intraperitoneal administration, which was more potent than ursolic acid and the reference drugs (ibuprofen and indomethacin). The cytotoxic activity of compound 3a was assessed in HeLa, Hep3B, and A549 cells.
650		4	\|a Ursolic acid
650		4	\|a Aminoguanidine
650		4	\|a Antibacterial activity
650		4	\|a Anti-inflammatory activity
650		4	\|a Cytotoxicity
700	1		\|a Ma, Song \|4 aut
700	1		\|a Zhang, Tian-Yi \|4 aut
700	1		\|a Wei, Zhi-Yu \|4 aut
700	1		\|a Wang, Hui-Min \|4 aut
700	1		\|a Guo, Fang-Yan \|4 aut
700	1		\|a Zheng, Chang-Ji \|4 aut
700	1		\|a Piao, Hu-Ri \|4 aut
773	0	8	\|i Enthalten in \|t Medicinal chemistry research \|d Springer US, 1991 \|g 28(2019), 7 vom: 27. Apr., Seite 959-973 \|h Online-Ressource \|w (DE-627)490223427 \|w (DE-600)2191978-1 \|w (DE-576)262493225 \|x 1554-8120 \|7 nnns
773	1	8	\|g volume:28 \|g year:2019 \|g number:7 \|g day:27 \|g month:04 \|g pages:959-973
856	4	0	\|u https://dx.doi.org/10.1007/s00044-019-02349-x \|z lizenzpflichtig \|3 Volltext
912			\|a GBV_USEFLAG_A
912			\|a SYSFLAG_A
912			\|a GBV_OLC
912			\|a FID-PHARM
912			\|a SSG-OPC-PHA
912			\|a GBV_ILN_11
912			\|a GBV_ILN_20
912			\|a GBV_ILN_22
912			\|a GBV_ILN_23
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_65
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_187
912			\|a GBV_ILN_213
912			\|a GBV_ILN_230
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_2070
912			\|a GBV_ILN_2086
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_2116
912			\|a GBV_ILN_2118
912			\|a GBV_ILN_2119
912			\|a GBV_ILN_2122
912			\|a GBV_ILN_2129
912			\|a GBV_ILN_2131
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_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_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
951			\|a AR
952			\|d 28 \|j 2019 \|e 7 \|b 27 \|c 04 \|h 959-973

Synthesis and biological evaluation of ursolic acid derivatives containing an aminoguanidine moiety

Zugang & Verfügbarkeit

Zugehörige Publikationen/Bände