42077-97-4Relevant academic research and scientific papers
The facile synthesis of 1-aminophosphonates from 1-nitrophosphonate precursors
Green, Donovan,Elgendy, Said,Patel, Geeta,Baban, Jehan A.,Skordalakes, Emmanuel,Husman, Wahid,Kakkar, Vijay V.,Deadman, John
, p. 303 - 306 (1996)
1-Aminophosphonates may be generated in high yield and spectroscopic purity by the treatment of 1-nitrophosphonates with LiBH4/Me3SiCl in THF at room temperature.
Direct access to enantiomerically enriched α-amino phosphonic acid derivatives by organocatalytic asymmetric hydrophosphonylation of imines
Pettersen, Daniel,Marcolini, Mauro,Bernardi, Luca,Fini, Francesco,Herrera, Raquel P.,Sgarzani, Valentina,Ricci, Alfredo
, p. 6269 - 6272 (2006)
A simple and efficient organocatalytic enantioselective hydrophosphonylation of imines to enantiomerically enriched α-amino phosphonates is reported. By using 10 mol % of quinine as the catalyst in the enantioselective addition of diethyl phosphite to N-B
Asymmetric synthesis of α-amino phosphonic acids employing versatile sulfinimines and sulfonimines
Lefebvre, Isabelle M.,Evans, Slayton A.
, p. 397 - 400 (1999)
The addition of metallophosphites to activated imino substrates such as sulfonimine 1 and sulfinimines 4 was successfully achieved. High diastereoselectivities and good yields were obtained with sulfinimine acceptors. The nucleophilic addition was applied to the development of a new methodology for the synthesis of enantiomerically homogeneous α-amino phosphonic acids.
Design, synthesis of novel celastrol derivatives and study on their antitumor growth through HIF-1α pathway
Shang, Fan-Fan,Wang, Jing Ying,Xu, Qian,Deng, Hao,Guo, Hong-Yan,Jin, Xuejun,Li, Xiaoting,Shen, Qing-Kun,Quan, Zhe-Shan
, (2021/05/03)
Four series of hypoxia-inducible factor-1 alpha (HIF-1α) functioning derivatives stemming from modifications to the C-29 carboxyl group of celastrol were designed and synthesized, and their anticancer activities were evaluated. To address the structure and activity relationship of each derivative, extensive structural changes were made. HRE luciferase reporter assay demonstrated that 12 modified compounds showed superior HIF-1α inhibitory activity. Among them, compound C6 exhibited the best features: firstly, the strongest HIF-1α inhibitory activity (IC50 = 0.05 μM, 5-fold higher than that of celastrol); secondly, lower cytotoxicity (22-fold lower, C6-16.85 μM vs celastrol-0.76 μM). Thus, the safety factor of C6 was about 112 times higher than that of celastrol. Western blot assay indicated that C6 may inhibit the expression of HIF-1α protein in cells. Additionally, C6 hindered tumor cell cloning, migration and induced cell apoptosis. It is worth mentioning that in the mouse tumor xenograft model, C6 (10 mg/kg) displayed good antitumor activity in vivo, showing a better inhibition rate (74.03%) than the reference compound 5-fluorouracil (inhibition rate, 59.58%). However, the celastrol treatment group experienced collective death after four doses of the drug. Moreover, C6 minimally affected the mouse weight, indicating that its application in vivo has little toxic effect. H&E staining experiments show that it could also exacerbate the degree of tumor cell damage. The results of water solubility experiment show that the solubility of C6 is increased by 1.36 times than that of celastrol. In conclusion, C6 is a promising antitumor agent through HIF-1α pathway.
Carbon Dioxide-Mediated C(sp2)-H Arylation of Primary and Secondary Benzylamines
Kapoor, Mohit,Chand-Thakuri, Pratibha,Young, Michael C.
supporting information, p. 7980 - 7989 (2019/05/22)
C-C bond formation by transition metal-catalyzed C-H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of ortho-arylbenzylamines, however, effective ortho-C-C bond formation of free primary and secondary benzylamines using PdII remains an outstanding challenge. Presented herein is a new strategy for constructing ortho-arylated primary and secondary benzylamines mediated by carbon dioxide (CO2). The use of CO2 with Pd is critical to allowing this transformation to proceed under relatively mild conditions, and mechanistic studies indicate that it (CO2) is directly involved in the rate-determining step. Furthermore, the milder temperatures furnish free amine products that can be directly used or elaborated without the need for deprotection. In cases where diarylation is possible, an interesting chelate effect is shown to facilitate selective monoarylation.
Design and synthesis of C-19 isosteviol derivatives as potent and highly selective antiproliferative agents
Luan, Tian,Cao, Li-Hua,Deng, Hao,Shen, Qing-Kun,Tian, Yu-Shun,Quan, Zhe-Shan
, (2019/01/16)
Six series of novel isosteviol derivatives; modified in the C-19 position; were synthesized; and their antiproliferative activity was evaluated against three human cancer cell lines (HCT-116; BEL-7402; HepG2) and the human L02 normal cell line in vitro. M
Synthesis and Biological Evaluation of (+)-Usnic Acid Derivatives as Potential Anti- Toxoplasma gondii Agents
Guo, Hong-Yan,Jin, Chun-Mei,Jin, Chunmei,Quan, Zhe-Shan,Shen, Qing-Kun,Zhang, Hai-Ming
, (2019/09/06)
Six series of (+)-usnic acid derivatives were synthesized. The IC50 values of these compounds were determined in T. gondii infected HeLa cells (μM) and in HeLa cells (μM), and their selectivity indexes (SI) were calculated. In vitro, most of th
Nickel-Catalyzed Hydrophosphonylation and Hydrogenation of Aromatic Nitriles Assisted by Lewis Acid
Islas, Rosa E.,García, Juventino J.
, p. 1337 - 1345 (2019/02/01)
In this paper, we describe the catalytic hydrophosphonylation of several aromatic nitriles used to synthesize α-aminophosphonates (α-APs) using commercially available trialkyl phosphites (P(OR)3, R=Et, iPr, Bu,) and simple and inexpensive nickel chloride (NiCl2.6H2O) as the catalytic precursor. The use of triethylborane (Et3B) as a Lewis acid (LA) was mandatory in order to successfully perform H-phosphite moiety incorporation at the CN bond of non-activated benzonitriles (BN) derivatives. Interestingly, when a highly activated BN such as 2,3,4,5,6-pentafluorobenzonitrile (BN-g) was employed, it was possible to perform the reaction in the absence of an LA using milder reaction conditions. Also, we found that using HP(O)(OiPr)2 as a starting material afforded the aminobisphosphonate derivative with better selectivity than using the method involving P(OiPr)3 as the initial reagent. Remarkably, when using HP(O)(OiPr)2 with an excess of Et3B, the reaction's selectivity completely changed to yield N-benzyl- benzylimine (BBI) and 2,4,5-triphenylimidazole.
One-Pot Two-Step Synthesis of Optically Active α-Amino Phosphonates by Palladium-Catalyzed Hydrogenation/Hydrogenolysis of α-Hydrazono Phosphonates
Goulioukina, Nataliya S.,Shergold, Ilya A.,Rybakov, Victor B.,Beletskaya, Irina P.
supporting information, p. 153 - 162 (2017/01/14)
An efficient and convenient one-pot procedure for the stereoselective catalytic synthesis of ring-substituted [amino(phenyl)methyl]phosphonates has been developed. The enantioselective hydrogenation of easily available diisopropyl (Z)-[aryl(phenylhydrazono)methyl]phosphonates using palladium(II) acetate as a precatalyst, (R)-2,2′-bis(diphenylphosphino)-5,5′-dichloro-6,6′-dimethoxy-1,1′-biphenyl [(R)-Cl–MeO-BIPHEP] as a ligand, and (1S)-(+)-10-camphorsulfonic acid as an activator in a mixture of 2,2,2-trifluoroethanol and methylene chloride at ambient temperature results in the formation of corresponding [aryl(2-phenylhydrazino)methyl]phosphonates. The subsequent cleavage of the N?N bond has been accomplished with molecular hydrogen after the addition of palladium on carbon and methanol into crude reaction mixture to afford the optically active [amino(aryl)methyl]phosphonates. The method is operationally simple and provides an appreciable enantioselectivity up to 98 % ee. (Figure presented.).
Improved facile synthesis of α-amino phosphonates by the reaction of α-amido sulfones with dialkyl trimethyl silyl phosphites catalyzed by Fe(III) chloride
Veeranjaneyulu, Boyapati,Das, Biswanath
, p. 449 - 456 (2017/02/24)
An improved efficient synthesis of α-amino phosphonates has been discovered by the reaction of N-benzyloxycarbonylamino sulfones with dialkyl trimethyl silyl phosphites in the presence of FeCl3as a catalyst. The products were formed in high yie
