189341-65-9Relevant academic research and scientific papers
Intermolecular 1,2-Difunctionalization of Alkenes Enabled by Fluoroamide-Directed Remote Benzyl C(sp3)-H Functionalization
Zhong, Long-Jin,Xiong, Zhi-Qiang,Ouyang, Xuan-Hui,Li, Yang,Song, Ren-Jie,Sun, Qing,Lu, Xin,Li, Jin-Heng
supporting information, p. 339 - 348 (2022/01/08)
A copper-catalyzed remote benzylic C-H functionalization strategy enabling 1,2-difunctionalization of alkenes with 2-methylbenzeneamides and nucleophiles, including alcohols, indoles, pyrroles, and the intrinsic amino groups, is reported, which is charact
Nickel-Catalyzed Enantioselective α-Alkenylation of N-Sulfonyl Amines: Modular Access to Chiral α-Branched Amines
Li, Lun,Liu, Yu-Cheng,Shi, Hang
supporting information, p. 4154 - 4161 (2021/04/06)
Chiral α-branched amines are common structural motifs in functional materials, pharmaceuticals, and chiral catalysts. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we describe an atom-economical, modular method for a nickel-catalyzed enantioselective α-Alkenylation of readily available linear N-sulfonyl amines with alkynes to afford a wide variety of allylic amines without the need for exogenous oxidants, reductants, or activating reagents. The method provides a platform for constructing chiral α-branched amines as well as derivatives such as α-Amino amides and β-Amino alcohols, which can be conveniently accessed from the newly introduced alkene. Given the generality, versatility, and high atom economy of this method, we anticipate that it will have broad synthetic utility.
Transition-Metal-Free One-Step Synthesis of Ynamides
Zeng, Xianzhu,Tu, Yongliang,Zhang, Zhenming,You, Changming,Wu, Jiao,Ye, Zhiying,Zhao, Junfeng
, p. 4458 - 4466 (2019/03/26)
A robust transition-metal-free one-step strategy for the synthesis of ynamides from sulfonamides and (Z)-1,2-dichloroalkenes or alkynyl chlorides is presented. This method is not only effective for internal ynamides but also amenable for terminal ynamides. Various functional groups, even the vinyl moiety, are compatible, and thus, this strategy offers the opportunity for further functionalization.
Synthesis and evaluation of unsymmetrical polyamine derivatives as antitumor agents
Wang, Jianhong,Xie, Songqiang,Li, Yanjie,Guo, Yongjun,Ma, Yuanfang,Zhao, Jin,Phanstiel IV, Otto,Wang, Chaojie
, p. 7005 - 7012 (2008/12/22)
A series of unsymmetrically substituted polyamine derivatives were prepared and their cytotoxicities in mouse leukemia L1210, melanoma B16, and HeLa cells were investigated. The in vitro cytotoxicity revealed that these conjugates could recognize the poly
A comparison of structure-activity relationships between spermidine and spermine analogue antineoplastics
Bergeron, Raymond J.,Feng, Yang,Weimar, William R.,McManis, James S.,Dimova, Hristina,Porter, Carl,Raisler, Brian,Phanstiel, Otto
, p. 1475 - 1494 (2007/10/03)
A systematic investigation of the impact of spermidine analogues both in vitro and in vivo is described. The study characterizes the effects of these analogues on L1210 cell growth, polyamine pools, ornithine decarboxylase, S- adenosyl-L-methionine decarboxylase, spermidine/spermine N1- acetyltransferase, the maintenance of cellular charge, i.e., cationic equivalence associated with the polyamines and their analogues, and compares their ability to compete with spermidine for transport. The findings clearly demonstrate that the activity of the linear polyamine analogues is highly dependent on the length of the triamines and the size of the N(α),N(ω)- substituents. It appears that there is an optimum chain length for various activities and that the larger the N(α)N(ω)-alkyls, the less active the compound. Metabolic transformation including N-dealkylation of these compounds is also evaluated. While there is no monotonic relationship between chain length and the ability of the analogue to be metabolized, the dipropyl triamines are clearly more actively catabolized than the corresponding methyl and ethyl systems. A comparison of the triamines with the corresponding tetraamines is made throughout the text regarding both in vitro activity against L1210 cells and in vivo toxicity measurements, suggesting that several triamine analogues may offer therapeutic advantages over the corresponding tetraamines.
