4055-69-0Relevant academic research and scientific papers
Synthesis and biological evaluation of 10-benzyloxy-Narciclasine
Ticli, Vincenzo,Zhao, Zhenze,Du, Liqin,Kornienko, Alexander,Hudlicky, Tomas
, (2021/11/08)
A chemoenzymatic convergent synthesis of 10-benzyloxy narciclasine from bromobenzene was accomplished in 16 steps. The key transformations included toluene dioxygenase-mediated hydroxylation, nitroso Diels-Alder reaction and intramolecular Heck cyclization. The unnatural derivative of narciclasine was subjected to biological evaluation and its activity was compared to other C-10 and C-7 compounds prepared previously.
N–H insertion reaction via an iron carbenoid from α-diazophenylpropionate and its application to the formal total synthesis of stizolobinic acid
Homma, Hiroki,Miyairi, Shinichi,Mizuta, Katsumi,Saito, Hiroaki,Shinohara, Hideyuki,Uchiyama, Taketo
, (2020/10/13)
The formal total synthesis of the non-proteinogenic amino acid stizolobinic acid was accomplished relying as key step on an iron carbenoid-based N–H insertion reaction. The N–H insertion of α-diazophenylpropionate and benzylamine derivative catalyzed by tetrakis(pentafluorophenyl)porphyrin iron (III) chloride afforded the desired N–H insertion product in 79% yield. This is the first example of an N–H insertion involving α-diazophenylpropionate and an aliphatic amine catalyzed by an iron(III) porphyrin complex.
Bioreductively Activatable Prodrug Conjugates of Combretastatin A-1 and Combretastatin A-4 as Anticancer Agents Targeted toward Tumor-Associated Hypoxia
Chaplin, David J.,Davis, Peter,Devkota, Laxman,Gerberich, Jeni L.,Hamel, Ernest,Kuch, Bunnarack,Macdonough, Matthew T.,Mason, Ralph P.,Mondal, Deboprosad,Pinney, Kevin G.,Ramirez, Alejandro J.,Shi, Zhe,Strecker, Tracy E.,Trawick, Mary Lynn,Wang, Yifan,Winn, Blake A.
, (2020/03/30)
The natural products combretastatin A-1 (CA1) and combretastatin A-4 (CA4) function as potent inhibitors of tubulin polymerization and as selective vascular disrupting agents (VDAs) in tumors. Bioreductively activatable prodrug conjugates (BAPCs) can enha
Synthetic methods for phoyunbenes A-D and thunalbene
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Paragraph 0026; 0027, (2017/04/13)
Invented is a method for synthesizing thunalbene and phoyunbenes A-D via a Horner-Wadsworth-Emmons (HWE) reaction in a simple and effective way. The compounds of the present invention have shown anti-inflammatory effects in RAW-264.7 macrophage which is induced by lipopolysaccharide.
3-substituted coumarin derivatives and their use
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Paragraph 0182; 0183; 0184, (2016/10/08)
The invention provides a 3-substituted coumarin derivative, and pharmaceutically acceptable salts, solvates, hydrates or crystal forms thereof. The above compound has a high calcium flow activity and a very good selectivity on a human derived cannabinoid receptor CB2, and is a specific agonist or inverse agonist of the cannabinoid receptor CB2. The compound is an active ligand of a novel cannabinoid II receptor CB2, and compounds of the above kind and pharmaceutically acceptable salts, solvates, hydrates or crystal forms thereof have high calcium flow activities and a very good selectivity on the human derived cannabinoid receptor CB2. The compound is the specific agonist or inverse agonist of the cannabinoid receptor CB2, and can be applied to the preparation of medicines for treating, preventing and inhibiting CB2 receptor mediated diseases. The structure of the derivative is represented by a general formula A shown in the specification.
Syntheses of phoyunbenes A-D and thunalbene for their anti-inflammatory evaluation
Moon, Insu,Kim, Jin-Kyung,Jun, Jong-Gab
, p. 2907 - 2914 (2016/01/25)
Simple and efficient first syntheses of phoyunbenes A-D and thunalbene have been developed using Horner- Wadsworth-Emmons reaction as a key step. Later, their anti-inflammatory effects were investigated in lipopolysaccharide-induced RAW-264.7 macrophages. The results revealed that phoyunbenes A-D and thunalbene showed weak inhibitory activities without cytotoxicity on the production of nitric oxide (NO) which is an important inflammatory mediator.
Design, syntheses, structure - Activity relationships and docking studies of coumarin derivatives as novel selective ligands for the CB2 receptor
Han, Shuang,Zhang, Fei-Fei,Qian, Hai-Yan,Chen, Li-Li,Pu, Jian-Bin,Xie, Xin,Chen, Jian-Zhong
, p. 16 - 32 (2015/03/05)
The CB2 receptor has been considered as an inspiring drug target for the treatment of pain and immune-related diseases. In the current manuscript, a novel series of coumarin derivatives is reported to be designed and synthesized by combining the structural features of some known ligands for the cannabinoid receptors based on the CoMFA model of the lead compounds. The compounds were evaluated to be highly selective ligands for the CB2 receptor over the CB1 receptor by calcium mobilization assays. Furthermore, SAR results Therefore, molecular docking simulations were performed to calculate the receptor-ligand interactions of our synthesized compounds binding to the CB2 receptor. The understanding of the binding modes could be advantageous for further development of selective ligands for the CB2 receptor.
Total syntheses of the coumarin-containing natural products pimpinellin and fraxetin using Au(I)-catalyzed intramolecular hydroarylation (IMHA) chemistry
Cervi, Aymeric,Aillard, Paul,Hazeri, Nourallah,Petit, Laurent,Chai, Christina L. L.,Willis, Anthony C.,Banwell, Martin G.
, p. 9876 - 9882 (2013/10/22)
The title natural products (1 and 2, respectively) have been synthesized by Au(I)-catalyzed intramolecular hydroarylation (IMHA) of the relevant aryl propiolate esters (e.g., 13), which were themselves formed by reaction of the corresponding phenols with either 3-(trimethylsilyl)propiolic acid or propiolic acid and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride or dicyclohexylcarbodiimide. (±)-Purpurasol (3) was readily derived from fraxetin (2) by established procedures.
Correlation of hydrogen-bonding propensity and anticancer profile of tetrazole-tethered combretastatin analogues
Jedhe, Ganesh S.,Paul, Debasish,Gonnade, Rajesh G.,Santra, Manas K.,Hamel, Ernest,Nguyen, Tam Luong,Sanjayan, Gangadhar J.
supporting information, p. 4680 - 4684 (2013/08/15)
A series of 1,5-disubstituted tetrazole-tethered combretastatin analogues with extended hydrogen-bond donors at the ortho-positions of the aryl A and B rings were developed and evaluated for their antitubulin and antiproliferative activity. We wanted to test whether intramolecular hydrogen-bonding used as a conformational locking element in these analogues would improve their activity. The correlation of crystal structures with the antitubulin and antiproliferative profiles of the modified analogues suggested that hydrogen-bond-mediated conformational control of the A ring is deleterious to the bioactivity. In contrast, although there was no clear evidence that intramolecular hydrogen bonding to the B ring enhanced activity, we found that increased substitution on the B ring had a positive effect on antitubulin and antiproliferative activity. Among the various analogues synthesized, compounds 5d and 5e, having hydrogen-bonding donor groups at the ortho and meta-positions on the 4-methoxy phenyl B ring, are strong inhibitors of tubulin polymerization and antiproliferative agents having IC50 value in micromolar concentrations.
Increased endothelial cell selectivity of triazole-bridged dihalogenated A-ring analogues of combretastatin A-1
Beale, Thomas M.,Bond, Peter J.,Brenton, James D.,Charnock-Jones, D. Stephen,Ley, Steven V.,Myers, Rebecca M.
experimental part, p. 1749 - 1759 (2012/04/10)
The antiproliferative activity on ovarian cancer (SK-OV-3) cells of a series of triazole-bridged combretastatin analogues (37, 38, 40-43) containing dihalogenation of the A-ring is reported, and compared with their trimethoxy analogues (5, 15, 39). It was found that dihalogenation with either bromine or iodine was a tolerated modification when compared to the parent compound combretastatin (CA-4, 1) and had less effect than B-ring modification on potency. These compounds exhibited G2/M arrest, and maintained antitubulin activity. Further assays on human umbilical vein endothelial cells (HUVECs) demonstrated the potential antivascular effects of these triazoles. Of particular note was a 3,5-diiodo-4-methoxyaryl triazole (43) which had promising 7-fold selectivity for HUVECs over ovarian cancer cells.
