- Synthesis of novel 4β-(1,2,3-triazol-1-yl) podophyllotoxins as potential antitumor drugs
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The synthesis, characterization and in vitro antitumor activity of two novel podophyllotoxins, 4β-(5-methyl-1,2,3-triazol-1-yl)podophyllotoxin (5) and 4β-(5-phenyl-1,2,3-triazol-1-yl)podophyllotoxin (6), are described.
- Tao, Lan,Wang, Yan-Guang,Ma, Cheng,Zheng, Bing,Chen, Yao-Zu
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- Synthesis and insecticidal activity of novel 4beta-halogenated benzoylamino podophyllotoxins against Pieris rapae Linnaeus.
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Twelve new 4beta-halogenated benzoylamino compounds (7.1-7.12) of podophyllotoxin have been synthesized, and their structures were confirmed by IR, 1H-NMR, MS spectra as well as CHN elemental analysis. These compounds showed delayed insecticidal activity
- Xu, Hui,Zhang, Xing,Tian, Xuan,Lu, Min,Wang, Yan-Guang
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- One-pot synthesis of podophyllotoxin-thiourea congeners by employing NH2SO3H/NaI: Anticancer activity, DNA topoisomerase-II inhibition, and apoptosis inducing agents
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A facile one-pot method for the synthesis of novel podophyllotoxin-thiourea congeners has been developed by using NH2SO3H/NaI system. Interestingly, 4β-azido podophyllotoxin reduction with concomitant aryl isothiocyanates coupling un
- Shankaraiah, Nagula,Kumar, Niggula Praveen,Amula, Suresh Babu,Nekkanti, Shalini,Jeengar, Manish Kumar,Naidu,Reddy, T. Srinivasa,Kamal, Ahmed
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- Synthesis, antitumor activity, and molecular docking of (?)-epigallocatechin-3-gallate-4β-triazolopodophyllotoxin conjugates
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Two new (?)-epigallocatechin-3-gallate-4β-triazolopodophyllotoxin conjugates (7 and 8) were synthesized and evaluated for biological activity. Compound 8 showed highly potent anticancer activity against A-549 cell line with IC50 of 2.16 ± 1.02
- Zi, Cheng-Ting,Yang, Liu,Hu, Yue,Zhang, Pan,Tang, Han,Zhang, Bang-Lei,Shen, Xiao-Jing,Kong, Qing-Hua,Wang, Ya,Wang, Xuan-Jun,Sheng, Jun
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p. 772 - 780
(2020/07/13)
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- Synthesis and Anticancer Activity of Podophyllotoxin Derivatives
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Two series of podophyllotoxin derivatives were synthesized by addition of a 4β-sulfanilamide to or substitution of a 4β-amide into podophyllotoxin. Their cytotoxicities were evaluated against four human cancer cell lines (A549, HeLa, MCF-7, and PC-3). Inv
- Bozorov, K.,Cao, J.,Dai, X.,Guo, H.,Huang, G.,Lin, K.,Ma, L.,Zhang, X.
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p. 1010 - 1018
(2021/11/30)
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- Synthesis and antitumor activity of camptothecin- 4β-triazolopodophyllotoxin conjugates
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Two new compounds (9 and 10) having a camptothecin (CPT) analog conjugated to the 4β-azido-4-deoxypodophyllotixin analog by untilizing the copper-catalyzed azide-alkyne cycloadditon (CuAAC) reaction, and were evaluated for their cytotoxicity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480) using the MTT (3-(4,5-dimethyl-thiahiazo-2-yl)-2,5-diphenyltetrazolium bromide) assay. Two novel conjugates shown weak cytotoxicity, compound 10 showed highly potent against HL-60 cell line tested, with IC50 value 17.69 ± 0.19 μM. This compound suggested its potential as anticancer agents for further development. (Figure presented.).
- Ding, Zhong-Tao,Dong, Fa-Wu,Hu, Jiang-Miao,Jiang, Zi-Hua,Kong, Qing-Hua,Yang, Liu,Zhou, Jun,Zi, Cheng-Ting
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supporting information
p. 2301 - 2309
(2019/01/19)
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- Synthesis and Cytotoxicity of Heterocyclic Amine Derivatives of Podophyllotoxin
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A series of amine podophyllotoxin derivatives was designed and synthesized by aldehydes reacting with 4β-amino-desoxypodophyllotoxin or 4′-demethyldesoxypodophyllotoxin. The MTT assay was used to test the cytotoxic activity of 11 target compounds on HeLa
- Chen, Hong,Liang, Chun-po,Luo, Gang,Tian, Dan-li
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p. 994 - 999
(2020/11/18)
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- Podophyllotoxin compound containing 1,2,4-triazone structure, and application thereof
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The invention discloses a podophyllotoxin compound containing a 1,2,4-triazone structure, and an application thereof. The compound has a structure represented by general formula (I). Podophyllotoxin derivatives containing 1,2,4-triazone, represented by th
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Paragraph 0042; 0043
(2018/03/26)
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- Synthesis and Biological evaluation of novel 4β-[(5-substituted)-1,2,3,4-tetrazolyl] podophyllotoxins as anticancer compounds
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A series of novel 4β-[(5-substituted)-1,2,3,4-tetrazolyl] podophyllotoxin derivatives were synthesized by employing azide-nitrile click chemistry approach. All the derivatives were evaluated for their cytotoxicity against a panel of four human cancer cell lines and their IC50 values were found to be in the range of 2.4-29.06 μM. The cytotoxicity exhibited by the majority of test compounds were found to comparable and often more effective than doxorubicin and all compounds exhibited higher cytotoxicity on A-549 cell lines. Cell cycle analysis showed that the novel 4β-[(5-substituted)-1,2,3,4-tetrazolyl] podophyllotoxins resulted in cell cycle arrest at G2/M phase and were also found to be the potent inhibitors of tubulin polymerization in vitro.
- Hyder, Irfan,Yedlapudi, Deepthi,Kalivendi, Shasi V.,Khazir, Jabeena,Ismail, Tabasum,Nalla, Naresh,Miryala, Sreekanth,Sampath Kumar, Halmuthur M.
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p. 2860 - 2863
(2015/06/08)
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- Differential Targeting of Human Topoisomerase II Isoforms with Small Molecules
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(Chemical Equation Presented). The TOP2 poison etoposide has been implicated in the generation of secondary malignancies during cancer treatment. Structural similarities between TOP2 isoforms challenge the rational design of isoform-specific poisons to further delineate these processes. Herein, we describe the synthesis and biological evaluation of a focused library of etoposide analogues, with the identification of two novel small molecules exhibiting TOP2B-dependent toxicity. Our findings pave the way toward studying isoform-specific cellular processes by means of small molecule intervention.
- Mariani, Angelica,Bartoli, Alexandra,Atwal, Mandeep,Lee, Ka C.,Austin, Caroline A.,Rodriguez, Rapha?l
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supporting information
p. 4851 - 4856
(2015/06/25)
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- Synthesis and evaluation of new podophyllotoxin derivatives with in vitro anticancer activity
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A series of novel podophyllotoxin derivatives were designed and synthesized. The cytotoxic activities of these compounds were tested against three tumor cell lines (HeLa, K562, and K562/A02). Most of the derivatives (IC50 = 1-20 μM) were found
- Cheng, Wei-Hua,Shang, Hai,Niu, Cong,Zhang, Zhong-Heng,Zhang, Li-Ming,Chen, Hong,Zou, Zhong-Mei
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p. 12266 - 12279
(2015/08/06)
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- Synthesis and biological evaluation of novel podophyllotoxin analogs as antitumor agents
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A series of 4β N-indole-substituted podophyllotoxin derivatives were synthesized. Nine target compounds were evaluated against human cancer cell lines (HeLa, K562, and K562/A02) using MTT assay including three imine derivatives 8, 9, and 10in vitro. The result showed that the three compounds had higher antitumor activity than their reduced forms. Among them, compounds 8, 9, 11, and 16 were superior to the positive control VP-16.
- Zhang, Zhong-Heng,Zhang, Li-Ming,Luo, Gang,Zhang, Shi,Chen, Hong,Zhou, Jing
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p. 527 - 534
(2014/06/09)
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- Design, synthesis and cytotoxic activity of novel sulfonylurea derivatives of podophyllotoxin
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Three series of novel sulfonylurea podophyllotoxin derivatives were designed, synthesized, and evaluated for in vitro cytotoxicity against four tumor cell lines (A-549, DU-145, KB and KBvin). Compounds 14c (IC50: 1.41-1.76 μM) and 14e (IC5
- Zhang, Zhi-Jun,Tian, Jing,Wang, Li-Ting,Wang, Mei-Juan,Nan, Xiang,Yang, Liu,Liu, Ying-Qian,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung
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supporting information
p. 204 - 210
(2014/01/17)
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- Toward synthesis of third-generation spin-labeled podophyllotoxin derivatives using isocyanide multicomponent reactions
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Spin-labeled podophyllotoxins have elicited widespread interest due to their far superior antitumor activity compared to podophyllotoxin. To extend our prior studies in this research area, we synthesized a new generation of spin-labeled podophyllotoxin an
- Kou, Liang,Wang, Mei-Juan,Wang, Li-Ting,Zhao, Xiao-Bo,Nan, Xiang,Yang, Liu,Liu, Ying-Qian,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung
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p. 282 - 288
(2014/03/21)
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- Synthesis and evaluation of novel podophyllotoxin derivatives as potential antitumor agents
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Cancer multidrug resistance (MDR) is a common cause of treatment failure in cancer patients. Increased expression of permeability glycoprotein (P-gp), which is also known as MDR-1, is the main cause of multidrug resistance. Podophyllotoxin derivatives hold great promise in the battle to overcome multidrug resistance, as they can induce cytotoxicity through multiple mechanisms. Here, we synthesized sixteen novel podophyllotoxin derivatives and evaluated their cytotoxicities in human cancer cell lines, HeLa, K562 and K562/A02. Some of these compounds were more potent than etoposide, a clinically relevant inhibitor of DNA repair enzymes. In particular, compound 5p exhibited the most potent activity toward drug-resistant K562/A02 cells, as it robustly inhibited tumor cell proliferation and induced apoptosis. Furthermore, preliminary investigation suggested that 5p inhibited the expression of MDR-1 in K562/A02 cells more effectively than etoposide.
- Cheng, Wei-Hua,Cao, Bo,Shang, Hai,Niu, Cong,Zhang, Li-Ming,Zhang, Zhong-Heng,Tian, Dan-Li,Zhang, Shi,Chen, Hong,Zou, Zhong-Mei
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p. 498 - 507
(2014/09/16)
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- Design, synthesis, and antitumor activity of novel podophyllotoxin derivatives as potent anticancer agents
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In order to find novel synthetic compounds with superior antitumor activity and overcome multidrug resistance, a series of novel 4β-N-substituted podophyllotoxin derivatives were synthesized under mild conditions with satisfactory yield. Nine novel podophyllotoxin derivatives were synthesized by linking 4β-amino-podophyllotoxin with aldehydes via the formation of a Schiff's base, and imines were reducted to secondary amines. These novel derivatives have been evaluated for cytotoxicity against human cancer cell lines Hela, K562, and K562/AO2. The results indicated that these compounds possess superior bioactivity (IC50 values were found at the range of 10 -6-10-8 mol/l) and weak multidrug resistance.
- Liu, Jing,Cao, Bo,Gao, Ying,Bai, Mei,Mei, Xin,Chen, Hong,Jiang, Yun-Gen,Huang, Da-Jiang
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p. 985 - 992
(2014/01/06)
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- Synthesis and cytotoxic activity on human cancer cells of carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin
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Carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin were synthesized by means of click chemistry, and their cytotoxicities against human cancer cell lines HL-60, A-549, HeLa, and HCT-8 were evaluated. Some compounds were more potent than the anticancer drug etoposide. 4′-O-Demethyl- 4β-[(4-hydroxymethyl)-1,2,3-triazol-1-yl]-4-deoxypodophyllotoxin cyclopentyl carbamate, the most potent compound, induced cell cycle arrest in the G2/M phase accompanied by apoptosis in A-549 cells. Furthermore, this compound inhibited the formation of microtubules in A-549 cells and caused the inhibition of DNA topoisomerase-II.
- Liu, Jian-Fei,Sang, Chun-Yan,Xu, Xiao-Hui,Zhang, Lin-Lin,Yang, Xuan,Hui, Lin,Zhang, Jin-Bang,Chen, Shi-Wu
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p. 621 - 628
(2013/07/27)
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- Synthesis and biological evaluation of novel 4β-(1,3,4-oxadiazole-2- amino)-podophyllotoxin derivatives
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A series of new 4β-(1,3,4-oxadiazole-2-amino)-podophyllotoxin derivatives were designed and synthesized. Their cytotoxicity in vitro against six tumor cell lines (DU-145, SGC-7901, A549, SH-SY5Y, HepG2 and HeLa) were evaluated by standard MTT assay. The p
- Ren, Jie,Wu, Lin,Xin, Wen Qun,Chen, Xin,Hu, Kun
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supporting information; experimental part
p. 4778 - 4782
(2012/08/13)
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- Synthesis and antitumor activity of novel aroylthiourea derivatives of podophyllotoxin
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A novel series of 4β-[(4-substituted) aroylthiourea] derivatives of podophyllotoxin were synthesized and their abilities to inhibit the growth of cancer cells were investigated by MTT assay. Compound 4a possessed the highest cytotoxicity on HepG2, A549 an
- Zhao, Yu,Wang, Chengniu,Wu, Zhonghua,Fang, Jinghuai,Zhu, Li
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scheme or table
p. 17 - 24
(2012/06/01)
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- Synthesis and antitumor activity of novel podophyllotoxin derivatives against multidrug-resistant cancer cells
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Seven novel 4-N-substituted podophyllotoxin derivatives with indole rings were prepared and evaluated for cytotoxicity against human cancer cell lines HeLa, KB, KBV, K562, and K562/AO2. Most of them demonstrated improved antitumor activity and weak multidrug resistance compared to the drugs currently available.
- Guo, Yong-En,Chen, Hong,Zuo, Song,Liu, Dai-Lin,Lu, Yan-Ling,Lv, Jing-Jing,Wen, Shao-Peng,Zhang, Tong-Cun
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scheme or table
p. 417 - 424
(2011/07/29)
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- Synthesis and cytotoxicity evaluation of novel podophyllotoxin derivatives
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Seven benzylamino derivatives of podophyllotoxin 8a-8g were synthesized and their chemical structures were confirmed by IR, 1H-NMR, 13C-NMR and ESI-MS spectral analyses. Their abilities to inhibit the growth of cancer cells A549, HCT-116 and HepG2, were investigated by MTT assay. Compound 8b possessed the highest cytotoxicity on cancer cell lines with average IC50 values of 3.8 μM. All we synthetic compounds were cytotoxic against three cancer cell lines at the micromolar range, indicating podophyllotoxin derivatives with structural modification of benzylamino possess potent antitumor activity. Seven benzylamino derivatives of podophyllotoxin (8a-8g) were synthesized and screened for cytoxic activity. All seven compounds possess promising antitumor activity, especially compound 8b. Copyright
- Chengniu, Wang,Zhonghua, Wu,Yu, Zhao,Chunyan, Ni,Xiaodong, Zhao,Li, Zhu
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scheme or table
p. 735 - 740
(2012/06/30)
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- NOVEL GEM-DIFLUORINATED C-GLYCOSIDE COMPOUNDS DERIVED FROM PODOPHYLLOTOXIN, THEIR PREPARATION AND THEIR APPLICATIONS
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The invention relates to a gem-difluoride glycoconjugated compound with formula (I): where R represents II or a benzyl, acetyl, benzoyl alkyl group, R1 and R2 may be identical or different and represent H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl, tertiobutyldiphenylsilyl protective group or an acetal group of the CR′R′ type, where R′ and R′ may be identical or different and represent H or an alkyl, aryl, benzyl or thiophene group, R3 represents H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl or tertiobutyldiphenylsilyl protective group, R4 represents OR″, NGR′GR′, N3, or a phthalimide, where R″ represents H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl or tertiobutyldiphenylsilyl protective group, GR′ and GR′ may be identical or different and represent II or an alkyl, benzyl, benzoyl, acetyl, alkyloxycarbonyl, allyloxycarbonyl or benzyloxycarbonyl group, R5 represents a free or protected hydroxyl group or a halogen, R6 represents H or an alkyl, acetyl, benzyl, PO3H or PO3Na group. It is applicable to the preparation of compounds that can be used particularly for the treatment of cancer.
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Page/Page column 7
(2009/12/28)
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- Design, synthesis and cytotoxicity of novel podophyllotoxin derivatives
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A series of novel podophyllotoxin derivatives were designed using association strategy and synthesized by coupling either podophyllotoxin (1) or 4β-amino podophyllotoxin (3) with substituted indol-3-yl-glyoxyl chlorides. Their structures were identified using spectroscopic techniques. These novel derivatives have been evaluated for cytotoxicity in vitro against four human cancer cell lines with comparison to the parent compounds 1, 3 and indibulin (2). Some of the compounds (7a, 7c) showed comparable cytotoxicity to that of podophyllotoxin.
- Yu, Peng-Fei,Chen, Hong,Wang, Jing,He, Chun-Xian,Cao, Bo,Li, Min,Yang, Na,Lei, Zhi-Yong,Cheng, Mao-Sheng
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scheme or table
p. 831 - 834
(2009/06/25)
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- Synthesis and anti-HIV-1 activities of novel podophyllotoxin derivatives
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In order to explore the range of biological activities of the podophyllotoxin compound class, a novel series of derivatives of podophyllotoxin, which were conjugates containing stavudine and different structural podophyllotoxin analogues, were designed, synthesized, and evaluated for their anti-HIV-1 activities in vitro. Among these compounds, 19d and 19c showed the highest anti-HIV-1 activities with EC50 values of 0.17 and 0.29 μM and TI values of 466.9 and 354.5, respectively.
- Chen, Shi-Wu,Wang, Yun-Hua,Jin, Yan,Tian, Xuan,Zheng, Yong-Tang,Luo, Du-Qiang,Tu, Yong-Qiang
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p. 2091 - 2095
(2008/02/02)
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- Nicotinoyl azide (NCA)-mediated Mitsunobu reaction: An expedient one-pot transformation of alcohols into azides
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A practical and simple method that allows preparation of azides from alcohols is described. The process involves oxyphosphonium-type activation and it is based upon the use of nicotinoyl azide (NCA), a cheap and easily accessible azide ion source.
- Papeo, Gianluca,Posteri, Helena,Vianello, Paola,Varasi, Mario
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p. 2886 - 2892
(2007/10/03)
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- Synthesis of 4beta-amido and 4beta-sulphonamido analogues of podophyllotoxin as potential antitumour agents.
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The new 4beta-amido analogues of podophyllotoxin or 4'-O-demethylepipodophyllotoxin have been prepared either by the coupling of 4beta-amino podophyllotoxin or 4beta-amino-4'-O-demethyl epipodophyllotoxin with the corresponding acids in presence of DCC in dichloromethane or by treating the appropriate acid chloride or sulphonyl chloride in presence of Et(3)N. These 4beta-amido and 4beta-sulphonamido derivatives of podophyllotoxin have been evaluated for their cytotoxicity against six human cancer cell lines. Some of these analogues have shown promising anticancer activity.
- Kamal, Ahmed,Ashwini Kumar,Arifuddin,Dastidar, Sunanda G
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p. 5135 - 5142
(2007/10/03)
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- A facile and efficient synthesis of 4β-aminopodophyliotoxins
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4β-amino-4-desoxypodophyllotoxin and 4β-amino-4'-desmethyl-4- desoxypodophyllotoxin have been synthesized by reduction of the corresponding 4β-azidopodophyllotoxin derivatives with samarium diiodide in excellent yields under convenient and mild conditions.
- Yu, Yong-Ping,Chen, Shao-Yuan,Wang, Yan-Guang,Chen, Yao-Zu
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p. 1967 - 1970
(2007/10/03)
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- Azepines by Photochemical Ring Enlargement of 9-Azidopodophyllotoxin- and 9-Azido-9'-demethylepipodophyllotoxin Derivatives
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The azepines 5a-5c were obtained by photochemical nitrene rearrangement of the azides 1e/1f and 4b/4c in cyclohexene, but not in other solvents.They are ring expansion products of podophyllotoxin (1a) and resemble steganacin (9), but show only low biological activity.The triazenes 7a/8a and the aziridine 8b are also less active than 1a. - Keywords: Podophyllotoxin / Podophyllotoxin azides / Nitrene rearrangement
- Laatsch, Hartmut,Ernst, Bernd Peter,Hoffmann, Dieter
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p. 1773 - 1778
(2007/10/03)
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- New nitrogen derivatives of podophyllotoxin and a novel access to dehydroanhydropicropodophyllin
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The new compounds podophyllotoxone oxime (3) and epipodophyllotoxin azide (5) were prepared. The known dehydroanhydropicropodophyllin (6) was unexpectedly obtained from podophyllotoxin (1) by treatment with TMSCl/NaI/MeCN.
- De Lima,Raslan,De Oliveira
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p. 2675 - 2683
(2007/10/02)
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- New compounds related to podophyllotoxin and congeners: synthesis, structure elucidation and biological testing.
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4-Azido, 4-amino, 4-amido and 4-alkoxy compounds related to the lignans podophyllotoxin and 4'-demethylepipodophyllotoxin have been synthesized, and their structures elucidated. The Ritter reaction was shown to be useful in the preparation of the 4-amido compounds with the required stereochemistry. A preparative method for 4-chloro-4-deoxypicrophyllotoxin, for which all earlier synthetic attempts resulted in the two dehydrated compounds, alpha- and beta-apopicropodophyllotoxin, was developed. Supplementary preliminary studies of the biological activities of some of the compounds were performed. All compounds had pronounced inhibitory effect on the in vitro growth of human cervical cancer cells and TC-mouse cells with 4-amino-4-deoxypodophyllotoxin and 4-azido-4-deoxypodophyllotoxin showing the highest activity. Alkaline elution studies indicate that the toxicity of the 4'-demethoxy derivatives is due to protein-mediated DNA nicking. None of the compounds were found to have antiviral effect against herpes simplex type 2 (HSV-2), human immunodeficiency (HIV), and cytomegalovirus (CMV) in doses not toxic to the cells.
- Hansen,Jensen,Willumsen,Norskov-Lauritsen,Ebbesen,Nielsen,Buchardt
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p. 1190 - 1200
(2007/10/02)
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