1228552-16-6Relevant academic research and scientific papers
Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization to Form Functionalized Hexahydropyrido[3,4- b]Indole
Chen, Yi,Gao, Lu,Song, Xuanyi,Song, Zhenlei
supporting information, p. 124 - 128 (2021/01/13)
A fluoride-promoted intramolecular Sakurai allylation of geminal bis(silyl) enamide with indolenine has been developed. The reaction facilitates an efficient cyclization to give hexahydropyrido[3,4-b]indoles in good yields with high diastereoselectivity. The resulted cis, trans-stereochemistry further enables the ring-closing metathesis (RCM) reaction of two alkene moieties, giving a tetracyclic N-hetereocycle widely found as the core structure in akuammiline alkaloids.
Fradcarbazole A compound and preparation method and application thereof
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Paragraph 0014, (2019/07/01)
The invention discloses a fradcarbazole A compound and a preparation method and application thereof. The fradcarbazole A compound is prepared from staurosporine or halogenated staurosporine which is subjected to a sulfur acylation reaction, a salt forming reaction together with iodomethane, a substitution reaction and a dehydrating cyclization reaction. The fradcarbazole A compound has very high selectivity and inhibitory activity on acute myeloid cell strains, namely MV4-11, with Flt3-ITD mutation, has a weak inhibiting effect on human peripheral blood mononuclear cells (PBMC), and can be developed to be an efficient and low-toxicity drug for preventing and treating leukemia.
Semisynthetic Derivatives of Fradcarbazole A and Their Cytotoxicity against Acute Myeloid Leukemia Cell Lines
Li, Mingpeng,Xu, Yanchao,Zuo, Mingxing,Liu, Wen,Wang, Liping,Zhu, Weiming
, p. 2279 - 2290 (2019/09/19)
Fourteen derivatives of the marine-derived fradcarbazole A were synthesized from staurosporine. Their structures were identified by NMR and high-resolution electrospray ionization mass spectrometry (HRESIMS). The derivatives were screened in vitro for antiproliferative activity against three human leukemic cell lines (MV4-11, HL-60, K562). All of the derivatives displayed cytotoxicity against the human FLT-3 internal tandem duplication (ITD) mutant acute myeloid leukemia (AML) cell line MV4-11 with IC50 values of 0.32-0.96 μM. The mechanism of action studies indicated that the most effective 3-chloro-5"-fluorofradcarbazole A (6) induced apoptosis of the MV4-11 cells and arrested the cell cycle at the G0/G1 phase. Furthermore, compound 6 can reduce the expression of FLT-3, CDK2, and c-kit. The results suggest that 3-chloro-5"-fluorofradcarbazole A (6) is a potential candidate for developing novel anti-AML agents in the future.
Method for preparing spiro2-diazido-indoline
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Paragraph 0056; 0057, (2016/10/09)
The invention provides a method for preparing a compound shown in the formula II (please see the formula in the description). The method includes the following step of making indole shown in the formula I (please see the formula in the description) react with a precursor and ceric ammonium nitrate in the inert atmosphere so that spiro2-diazido-indoline can be obtained, wherein the precursor can provide azide groups. In the formula I and the formula II, R1 is selected from at least one of hydrogen, an alkyl group of C1-C5, alkoxy of C1-C5, F, Br and Cl; R2 is an alkyl group of C1-C5; Boc represents t-butyloxycarboryl. The precursor is sodium azide or trimethylsilyl azide. The mole ratio of indole shown in the formula I to the precursor to ceric ammonium nitrate is 1:(2-4):(4-8). According to the simple method, the two azide groups are introduced to the organic molecule, and in other words, spiro2-diazido-indoline is effectively prepared under the effects of the precursor capable of providing the azide groups and ceric ammonium nitrate with indole of different structures as the raw material. The raw material is easy to prepare, the reaction condition is gentle, operation is easy and convenient, and yield can reach 45% at most.
