1449601-57-3Relevant articles and documents
Efficient halogenation synthesis method of aryl halide
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Paragraph 0270-0274, (2021/03/31)
The invention discloses an efficient halogenation synthesis method of aryl halide. The method comprises the following step: in the presence of a catalyst (sulfoxide or oxynitride), a halogenation reagent and a solvent, carrying out a halogenation reaction on an aromatic ring compound to obtain the aryl halide. According to the present invention, in the presence of a catalyst (sulfoxide or nitrogenoxide), a halogenation reagent and a solvent, the aromatic ring is subjected to an efficient halogenation reaction, such that the very useful aryl halide can be obtained with high activity and high selectivity; and by adopting the method disclosed by the invention, aryl halides can be efficiently synthesized, and the method has a wide application prospect in actual production.
Synthesis and evaluation of etoposide and podophyllotoxin analogs against topoisomerase IIα and HCT-116 cells
Barton, Christopher E.,Bradley, Amber M.,Deweese, Joseph E.,Kumar, Priyanka,Mercer, Susan L.,Murphy, Matthew B.
supporting information, (2020/10/12)
Etoposide is a widely-used anticancer agent that targets human type II topoisomerases. Evidence suggests that metabolism of etoposide in myeloid progenitor cells is associated with translocations involved in leukemia development. Previous studies suggest
Synthesis of 2′(2′,6′)-(di)halogenoisoxazolopodophyllic acids-based amides derived from a naturally occurring lignan podophyllotoxin and their acaricidal activity
Zhang, Bingchuan,Yu, Mingqiao,Lv, Min,Xu, Hui
, p. 541 - 549 (2019/07/31)
In continuation of our program to discover natural product-based pesticides, a series of 2′(2′,6′)-(di)halogenoisoxazolopodophyllic acids-based amides were prepared by structural modification of a naturally occurring lignan podophyllotoxin. Meanwhile, the
Synthesis of novel isoxazoline-containing podophyllotoxin/2′(2′,6′)-(di)halogenopodophyllotoxin derivatives and their insecticidal/acaricidal activities
Yang, Ruige,Zhang, Yuanyuan,Xu, Hui
, p. 1410 - 1416 (2018/03/21)
In continuation of our program aimed at the development of natural product-based pesticidal agents, a series of isoxazoline-containing podophyllotoxin/2′(2′,6′)-(di)halogenopodophyllotoxin derivatives were prepared, and their structures were well characte
4 α-acyloxy -2 the [...] (2 the [...], the 6 [...] ), 2 α-halogenated podophyllotoxin derivatives, and their preparation and use
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Paragraph 0046-0047, (2017/02/28)
The invention discloses a series of new 4alpha-acyloxy-2'(2',6'),2alpha-polyhalogenated podophyllotoxin derivatives and a preparation method thereof. The chemical general formula of the series of 4alpha-acyloxy-2'(2',6'),2alpha-polyhalogenated podophyllot
Stereoselective synthesis of 2α-chloropicropodophyllotoxins and insecticidal activity of their esters against oriental armyworm, mythimna separata walker
Fan, Lingling,Guo, Yong,Zhi, Xiaoyan,Yu, Xiang,Xu, Hui
, p. 3726 - 3733 (2014/05/20)
As part of ongoing efforts to discover new natural-product-based insecticidal agents, in the present study, an efficient method for the stereoselective α-chlorination at the C-2 position of 2′(2′, 6′)-(di)halogenopodophyllotoxin derivatives was first developed. Subsequently, a series of novel esters of 2α-chloro-2′(2′, 6′)-(di)halogenopicropodophyllotoxin with modified C, D, and E rings of podophyllotoxin were smoothly obtained. Finally, all of the title compounds were tested against the pre-third-instar larvae of oriental armyworm (Mythimna separata Walker) at 1 mg/mL. It was found that besides their 2′-halogen-substituted E ring, the stereoselective α-chlorination at the C-2 position of 2′(2′,6′)-(di)halogenopodophyllotoxins was also related to the chlorination reagents. Especially 2α-chloro- 4α-(benzoyl)oxy-2′-chloropicropodophyllotoxin (6e) and 2α-chloro-4α-(2-chlorophenylacyl)oxy-2′- bromopicropodophyllotoxin (8f) showed the most potent insecticidal activities, with final mortality rates of >60%. For 4α-(alkylacyl)oxy derivatives of 2α-chloro-2′(2′,6′)-(di)halogenopicropodophyllotoxin, the effect of the length of their side chain at the C-4 position of podophyllotoxin skeleton on the insecticidal activity was not very obvious. For 4α-(arylacyl)oxy derivatives of 2α-chloro-2′-chloro/ bromopicropodophyllotoxin, an electronic effect of the substituents on their phenyl ring at the C-4 position of podophyllotoxin skeleton on the insecticidal activity was observed.
Stereoselective synthesis of 2α-chloropicropodophyllotoxins and insecticidal activity of their esters against oriental armyworm, Mythimna separata walker
Fan, Lingling,Guo, Yong,Zhi, Xiaoyan,Yu, Xiang,Xu, Hui
, p. 3726 - 3733 (2015/04/22)
As part of ongoing efforts to discover new natural-product-based insecticidal agents, in the present study, an efficient method for the stereoselective α-chlorination at the C-2 position of 2'(2',6')-(di)halogenopodophyllotoxin derivatives was first devel
Insight into dihalogenation of E-ring of podophyllotoxins, and their acyloxyation derivatives at the C4 position as insecticidal agents
Che, Zhiping,Yu, Xiang,Fan, Lingling,Xu, Hui
supporting information, p. 5592 - 5598 (2013/10/01)
Unexpected sequential E-ring dihalogenation of podophyllotoxin analogues is reported. It demonstrated that a chlorine/bromine atom was prior introduced at the C2′ position of podophyllotoxin, and the corresponding free rotation of E-ring around the C1-C1′
Synthesis of novel 4α-(Acyloxy)-2′(2′,6′)-(di) halogenopodophyllotoxin derivatives as insecticidal agents
Che, Zhiping,Yu, Xiang,Zhi, Xiaoyan,Fan, Lingling,Yao, Xiaojun,Xu, Hui
, p. 8148 - 8155 (2013/09/23)
In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, we have prepared three series of novel 4α-(acyloxy)-2′(2′,6′)-(di)halogenopodophyllotoxin derivatives modified in the C and E rings of podophyllotoxin, which is a naturally occurring aryltetralin lignan isolated from the roots and rhizomes of Podophyllum hexandrum. Their structures were well characterized by 1H NMR, HRMS, ESI-MS, optical rotation, and mp. The stereochemical configurations of compounds 5s, 6b, 6d, and 7q were unambiguously confirmed by single-crystal X-ray diffraction. Their insecticidal activity was evaluated against the pre-third-instar larvae of oriental armyworm, Mythimna separata Walker, in vivo at a concentration of 1 mg/mL. These derivatives likely displayed the antimolting hormone effect. Among all the derivatives, especially compounds 5a, 5n, 7f, 7n, and 7w exhibited the most potent insecticidal activity with final mortality rates of 70% or so. This suggested that a chlorine or bromine atom introduced at the C2′ or C2′ and C6′ positions on the E ring of podophyllotoxin was necessary for obtaining the potent compounds. This will pave the way for further design, structural modification, and development of podophyllotoxin derivatives as insecticidal agents.
