Synthesis, cytotoxic activity evaluation and HQSAR study of novel isosteviol derivatives as potential anticancer agents

Liu, Cong-Jun; Yu, Shuling; Liu, Yan-Ping; Dai, Xing‐Jie; Wu, Yangjie; Li, Ruijun; Tao, Jing‐Chao

doi:10.1016/j.ejmech.2016.03.009

Cited by 38 publications

(29 citation statements)

References 43 publications

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“…In this regard, interferon (IN)-a and nucleoside derivatives were developed [108]. Yet the low-to-moderate efficacy, unwanted side-effects, and drug resistant viral strains make this problem worse [109]. Considering these continuing efforts for the synthesis of new antiviral agents with novel targets and mechanisms to eradicate HBV.…”

Section: Pharmacological Activities Of Isosteviol Derivativesmentioning

confidence: 99%

“…Considering these continuing efforts for the synthesis of new antiviral agents with novel targets and mechanisms to eradicate HBV. Several isosteviol derivatives were prepared by replacing the 19-COOH with the ureide moiety, and their inhibitory action against HBV was evaluated [109]. Among them, NC-8 ent -16-oxobeyeran 19-N-methylureido, showed inhibitory activity against HBV and specifically inhibited viral gene expression and reduced the level of encapsulated viral DNA intermediates in Huh7 cells that expressed the replicating HBV [110].…”

Section: Pharmacological Activities Of Isosteviol Derivativesmentioning

confidence: 99%

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Bioactivity Profile of the Diterpene Isosteviol and its Derivatives

et al. 2019

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Steviosides, rebaudiosides and their analogues constitute a major class of naturally occurring biologically active diterpene compounds. The wide spectrum of pharmacological activity of this group of compounds has developed an interest among medicinal chemists to synthesize, purify, and analyze more selective and potent isosteviol derivatives. It has potential biological applications and improves the field of medicinal chemistry by designing novel drugs with the ability to cope against resistance developing diseases. The outstanding advancement in the design and synthesis of isosteviol and its derivative has proved its effectiveness and importance in the field of medicinal chemical research. The present review is an effort to integrate recently developed novel drugs syntheses from isosteviol and potentially active pharmacological importance of the isosteviol derivatives covering the recent advances.

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Section: Pharmacological Activities Of Isosteviol Derivativesmentioning

confidence: 99%

Section: Pharmacological Activities Of Isosteviol Derivativesmentioning

confidence: 99%

Bioactivity Profile of the Diterpene Isosteviol and its Derivatives

et al. 2019

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“…A noticeable cytotoxic potential of mentioned thiourea-derived compounds was observed against a wide range of solid tumors, such as breast [ 4 , 6 , 17 , 21 , 23 , 32 , 33 ], lung [ 4 , 20 , 22 , 23 , 27 , 29 , 31 , 34 ], liver [ 5 ], prostate [ 4 , 18 , 31 , 32 , 33 ], cervical [ 4 , 29 , 30 ], brain [ 20 , 24 , 29 ], gastric [ 25 ], or colon [ 27 , 29 , 35 ] carcinoma, as well as human leukemia [ 29 ]. Simultaneously some of them, when tested on normal human cells, were found to possess a low cytotoxicity profile [ 1 , 17 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

“…The main structural element of anticancer active thioureas were the presence of “the butterfly-like” tricyclic ring of acridine [ 29 ] or other heterocycles, such as pyrimidine [ 5 , 6 , 21 ], quinoline [ 27 ], quinazoline [ 22 , 23 ], furane [ 32 ], benzimidazole [ 4 ], chrysene [ 33 ], benzodioxole [ 18 ], triazole [ 17 ] or thiazole [ 20 ]. On the other hand, the most promising functionalities of a terminal aromatic ring were mainly electron-withdrawing substituents, such as nitro [ 27 , 33 , 35 ], cyano [ 17 ], trifluoromethyl/methoxy [ 17 , 19 ], halogeno [ 5 , 20 , 22 , 23 ], but also electron-withdrawing—methoxy [ 18 , 21 , 25 ] and methyl [ 24 ] groups. Among them, compounds containing the nitro group attached to the aromatic moiety (e.g., nitrofurans, bisnaphthalimides) are typically used as antibiotics and antimicrobials [ 36 , 37 ].…”

Section: Introductionmentioning

confidence: 99%

Disubstituted 4-Chloro-3-nitrophenylthiourea Derivatives: Antimicrobial and Cytotoxic Studies

et al. 2018

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4-Chloro-3-nitrophenylthioureas 1–30 were synthesized and tested for their antimicrobial and cytotoxic activities. Compounds exhibited high to moderate antistaphylococcal activity against both standard and clinical strains (MIC values 2–64 μg/mL). Among them derivatives with electron-donating alkyl substituents at the phenyl ring were the most promising. Moreover, compounds 1–6 and 8–19 were cytotoxic against MT-4 cells and various other cell lines derived from human hematological tumors (CC50 ≤ 10 μM). The influence of derivatives 11, 13 and 25 on viability, mortality and the growth rate of immortalized human keratinocytes (HaCaT) was observed.

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“…Furthermore, the cytotoxic activities of isosteviol derivatives have attracted much attention in recent years. In the previous study, the C-15 and C-16 functionalized isosteviol derivatives, obtained by means of group-conversion or structural modification exhibited good cytotoxic activities [17,18,19,20,21,22,23,24]. In view of the low cytotoxicity of isosteviol, it is suitable for the development of highly selective anticancer drugs by chemical modification [14,15,16].…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of C-19 Isosteviol Derivatives as Potent and Highly Selective Antiproliferative Agents

et al. 2018

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Six series of novel isosteviol derivatives; modified in the C-19 position; were synthesized; and their antiproliferative activity was evaluated against three human cancer cell lines (HCT-116; BEL-7402; HepG2) and the human L02 normal cell line in vitro. Most of the derivatives tested here exhibited improved antiproliferative activity with high selectivity when compared with the parent compound isosteviol and the positive control drug 5-fluorouracil. Among these derivatives; compound 5d exhibited the most potent antiproliferative activity and commendable selectivity between cancer and normal cells. In addition; compound 5d inhibited the colony formation of HCT-116 cells in a concentration-dependent manner. Further studies revealed that compound 5d arrested the HCT-116 cell cycle in the S phase; and western blot analysis demonstrated the mechanism may be correlated with a change in the expression of cyclin A; cyclin B1; and cyclin E1. Furthermore; the results of a docking study that involved placing compound 5d into the CDK2/cyclin A binding site revealed that its mode of action was possibly as a CDK2/cyclin A inhibitor.

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Synthesis, cytotoxic activity evaluation and HQSAR study of novel isosteviol derivatives as potential anticancer agents

Cited by 38 publications

References 43 publications

Bioactivity Profile of the Diterpene Isosteviol and its Derivatives

Bioactivity Profile of the Diterpene Isosteviol and its Derivatives

Disubstituted 4-Chloro-3-nitrophenylthiourea Derivatives: Antimicrobial and Cytotoxic Studies

Design and Synthesis of C-19 Isosteviol Derivatives as Potent and Highly Selective Antiproliferative Agents

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