871315-34-3

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 762-04-9 phosphonic acid diethyl ester 
• 119208-80-9 1,3,5-tris(4-methoxyphenyl)-2,4-diazapenta-1,4-diene 
• 45821-44-1 4-methoxy-benzylideneamine 

Downstream Products

• 1533457-23-6 diethyl ((S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanamido)(4-methoxyphenyl)methylphosphonate 
• 1454614-94-8 C₃₃H₄₇N₂O₅PS 
• 110470-34-3 diethyl [1-amine(4-methoxyphenyl)methyl]phosphonate 

Relevant academic research and scientific papers

Design, synthesis of novel celastrol derivatives and study on their antitumor growth through HIF-1α pathway

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.

Synthesis and antitumor activities of novel rhein α-aminophosphonates conjugates

Several rhein α-aminophosphonates conjugates (5a-5q) were synthesized and evaluated for in vitro cytotoxicity against HepG-2, CNE, Spca-2, Hela and Hct-116 cell lines. Some compounds showed relatively high cytotoxicity. Especially, compound 5i exhibited t

Coumarin-containing aminophosphonates bridged with chiral side chain: Synthesis and influence of chirality on cytotoxicity and DNA binding

A series of novel coumarin-containing α-Aminophosphonates with two chiral centers were synthesized and a single-crystal structure of compound 8g (8g', (R)-diethyl ((S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanamido)(2- bromophenyl)methylphosphonate) was

Synthesis and antitumor activities of novel diacerein α-aminophosphonates conjugates

Several diacerein α-aminophosphonates conjugates 4a-k have been synthesized, the structures of compounds have been characterized by IR, 1H NMR, 13C NMR, 31P NMR, ESI-MS spectra and elementary analysis. In vitro cytotoxicity against HepG-2, CNE, Spca-2 and Hct-116 cells are evaluated and employing standard MTT assay in comparing with commercial anticancer drug 5-fluorouracil (5-FU). Some compounds exhibit moderate to high levels of antitumor activity. Especially, compound 4i exhibit the strongest cytotoxicity against Hct-116 cells with IC50 9.83 μM. All the synthesized compounds exhibit low cytotoxicity against HUVEC cells. The mechanism of compound 4i has been preliminarily investigated by Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining and flow cytometry, which indicate that the compound 4i induced apoptosis in Hct-116 cancer cells. Cell cycle analysis show that compound 4i mainly arrested Hct-116 cells in G1 stage. The effects of 4i on the activation of caspases expression indicate that 4i might induce apoptosis via the membrane death receptor pathways. In addition, the binding properties of a model analog 4i to DNA have been investigated by methods (UV-Vis, fluorescence, CD spectroscopy) in comparison with that of diacerein. Results indicate that 4i show moderate ability to interact ct-DNA.

Synthesis and antitumor activities of novel α-aminophosphonates dehydroabietic acid derivatives

A series of novel α-aminophosphonate derivatives containing DHA structure were designed and synthesized as antitumor agents. In vitro antitumor activities of these compounds against the NCI-H460 (human lung cancer cell), A549 (human lung adenocarcinoma ce

Synthesis and cytotoxicity of O,O′-dialkyl {[2-(substituted phenoxy)acetamido](substituted phenyl)methyl}phosphonates

A series of O,O′-dialkyl {[2-(substituted phenoxy)acetamido] (substituted phenyl)methyl}phosphonates was synthesized and their cytotoxic activities were tested against various human tumor cell lines. Some compounds (5q, 5r, 5s, 5w, 5x and 5y) showed relatively high cytotoxicity. Especially, compounds 5x and 5q exhibited the best cytotoxicity against KB and CNE2 cells with IC50 7.1 and 11.4 μM, respectively. Their inhibitory activities against KB and CNE2 cells were even higher than that of fluorouracil.

Synthesis and biological evaluation of novel phosphonates derivatives of as potential antitumor agents

A series of dialkyl [2-(4,6-dimethoxypyrimidin-2-yloxy)benzamido](aryl) methylphosphonates derivatives were designed and synthesized. All the new compounds were identified by elemental analysis, IR, 1H NMR, 31P NMR, and MS. Their antitumor activity against KB and CNE1 cells was examined. Some of the compounds showed potential antitumor activity, which provided some hints for further study of structure modification. In particular, the compounds 6i and 6j displayed more potent cytotoxic activities against KB in comparison with 5-FU. Copyright Taylor & Francis Group, LLC.

Synthesis of a novel class of β-lactam derivatives of 1-aminophosphonates by staudinger ketene-imine [2+2]-cycloaddition reaction

A novel class of β-lactam derivatives of 1-aminophosphonates was synthesized by Staudinger [2+2] cycloaddition reaction of ketenes with imines derived from 1-aminophosphonates. Treatment of aromatic aldehydes with ammonia and diethyl phosphite followed by

Molecular iodine: An efficient catalyst for the one-pot synthesis of primary 1-aminophosphonates

A new and convenient procedure has been developed for the one-pot synthesis of different types of primary 1-aminophosphonates from aldehydes/ketones, HMDS and diethyl phosphite using I2 as an inexpensive, non-toxic, non-metallic and readily available cata

Synthesis and herbicidal activity of O,O-diethyl N-{4-Methyl-[1,2,3] thiadiazole-5-carbonyl}- 1-amino-1-substitutedbenzyl phosphonates

Target compounds 3 were synthesized by the condensation of O,O-diethyl α-amino substitutedbenzyl phosphonates 1 and 4-methyl-[1,2,3]thiadiazole- 5-carboxylic acid 2 in the presence of dicyclohexylcarbodiimide (DCC) as a dehydration reagent. Their structures were confirmed by spectroscopic data (IR, 1H NMR, 31P NMR, MS) and elemental analysis. The results of a preliminary bioassay (in vitro) indicated that some of the title compounds 3 possessed moderate to good herbicidal activities against dicotyledonous plants (Brassica campestris L) at the concentration of 100 mg/L, and most of these compounds exhibited higher herbicidal activities against dicotyledonous plants (Brassica campestris L) than monocotyledonous plants (Echinochloa crus-galli). Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright Taylor & Francis Group, LLC.