Synthesis, in vitro antimicrobial and cytotoxic activities of new carbazole derivatives of ursolic acid

Gu, Wen; Huang, Yun; Zhang, Guang; Wang, Shifa; Miao, Tingting; Zhang, Kang-Ping

doi:10.1016/j.bmcl.2014.12.021

Cited by 53 publications

(42 citation statements)

References 31 publications

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“…Prompted by the above facts, Gu et al (2015) synthesized a series of novel carbazole derivatives of UA (compounds 40-46, Table 4). Among these derivatives, some compounds showed significant cytotoxic activity to HepG2 cells with IC 50 values below 10 lM.…”

Section: Introductionmentioning

confidence: 99%

Anti-hepatocellular carcinoma activity and mechanism of chemopreventive compounds: ursolic acid derivatives

Huang

Chen

Ren

et al. 2016

Pharmaceutical Biology

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Context: Hepatocellular carcinoma (HCC) is a common cancer around the world, with high mortality rate. Currently, there is no effective drug for the therapy of HCC. Ursolic acid (UA) is a natural product which exists in various medicinal herbs and fruits, exhibiting multiple biological effects such as its outstanding anticancer and hepatoprotective activity, which has drawn many pharmacists' attention. Objective: This paper summarizes the current status of the hepatoprotective activity of UA analogues and explains the related mechanism, providing a clear direction for the development of novel anti-HCC drugs. Methods: All of the data resources were derived from PubMed. By comparing the IC 50 values and analyzing the structure-activity relationships, we listed compounds with good pharmacological activity from the relevant literature, and summarized their anti-HCC mechanism. Results: From the database, 58 new UA derivatives possessing wonderful anticancer and hepatoprotective effects were listed, and the relevant anti-HCC mechanism were discussed. Conclusion: UA's anti-HCC effect is the result of combined action of many mechanisms. These 58 new UA derivatives, particularly compounds 45 and 53, can be used as potential drugs for the treatment of liver cancer. ARTICLE HISTORY

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Section: Introductionmentioning

confidence: 99%

Anti-hepatocellular carcinoma activity and mechanism of chemopreventive compounds: ursolic acid derivatives

Huang

Chen

Ren

et al. 2016

Pharmaceutical Biology

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“…2,3-Indolo-12-oxo-oleanolic acid showed significant inhibition activity towards protein tyrosine phosphatase 1B [5]. The IC 50 value of ursolic acid modified with 5-methylindole moiety was comparable to doxorubicin [6], and the chloro-derivative of indolo-betulinic acid was found to be very active towards several cancer cell lines [7]. According to previous reports, some indolo-fused lupanes showed α-glucosidase inhibitory activity [8][9][10].…”

Section: Introductionmentioning

confidence: 83%

“…[3,2b]Indolo-N-prop-2-yn-1-yl-28-oxo-allobetulon(6) Compound 6 was obtained from compound 4 (0.53 g; 1 mmol) by a procedure similar to the synthesis of compound 5 as a yellow powder (0.40 g, 70%):[α] 20 D +80 (c 0.75, CH 2 Cl 2 ), m.p. 156 • C.1 H-NMR (δ, ppm, CDCl 3 , 500 MHz): 7.49−7.02 (4H, m, arom), 5.02 (2H, s, CH 2 ), 4.02 (1H, s, H-19), 2.92−2.82 (2H, m, CH 2 ), 1.88 (1H, s, C≡CH), 2.23−1.00 (20H, m, CH, CH 2 ), 1.42, 1.28, 1.18, 1.00, 0.95, 0.88, 0.85 (21H, all s, 7CH 3 ).…”

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confidence: 99%

N-Propargylation of Indolo-Triterpenoids and Their Application in Mannich Reaction

Khusnutdinova

Petrova

Bashirova

et al. 2019

Molbank

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“…For example, Staphylococcus aureus is a pathogen responsible for the main causes of in-hospital mortality [ 7 ]. Therefore, the discovery of new novel potent antibacterial and antitumor chemical entities is challenging work for medicinal chemists [ 8 , 9 , 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Activity, and Apoptotic Properties of NO-Donor/Enmein-Type ent-Kauranoid Hybrids

Han

et al. 2016

IJMS

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Herein, we reported on a series of synthetic nitric oxide-releasing enmein-type diterpenoid hybrids (9a–i). All the target compounds showed potent antibacterial activity against selected Gram-positive bacteria S. aureus and B. subtilis. The antiproliferative activity against human tumor K562, MGC-803, CaEs-17 and Bel-7402 cells, and human normal liver cells L-02 was tested and the structure activity relationships (SARs) were also concluded. Compounds 9b and 9d showed the best activity against S. aureus and B. subtilis with the same minimal inhibitory concentrations (MICs) of 4 and 2 μg/mL, respectively. The derivative 9f displayed IC50 values of 1.68, 1.11, 3.60 and 0.72 μM against the four cancer cell lines above and 18.80 μM against normal liver cells L-02; meanwhile, 9f also released a high level of NO at the time point of 60 min of 22.24 μmol/L. Furthermore, it was also found that 9f induced apoptosis via the mitochondria-related pathway and arrested cell cycle of Bel-7402 cells at S phase. These findings might be important to explore new chemical entities for the main causes of in-hospital mortality of S. aureus infection, combined with a solid tumor.

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Synthesis, in vitro antimicrobial and cytotoxic activities of new carbazole derivatives of ursolic acid

Cited by 53 publications

References 31 publications

Anti-hepatocellular carcinoma activity and mechanism of chemopreventive compounds: ursolic acid derivatives

Anti-hepatocellular carcinoma activity and mechanism of chemopreventive compounds: ursolic acid derivatives

N-Propargylation of Indolo-Triterpenoids and Their Application in Mannich Reaction

Synthesis, Biological Activity, and Apoptotic Properties of NO-Donor/Enmein-Type ent-Kauranoid Hybrids

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