4797-81-3Relevant academic research and scientific papers
Novel fluorinated 7-hydroxycoumarin derivatives containing an oxime ether moiety: Design, synthesis, crystal structure and biological evaluation
Dai, Peng,Jiao, Jian,Wang, Qing-Qing,Zhang, Shu-Guang,Zhang, Wei-Hua
, (2021/06/28)
A series of fluorinated 7-hydroxycoumarin derivatives containing an oxime ether moiety have been designed, synthesized and evaluated for their antifungal activity. All the target compounds were determined by1H-NMR,13C-NMR, FTIR and HR-MS spectra. The single-crystal structures of compounds 4e, 4h, 5h and 6c were further confirmed using X-ray diffraction. The antifungal activities against Botrytis cinerea (B. cinerea), Alternaria solani (A. solani), Gibberella zeae (G. zeae), Rhizoctorzia solani (R. solani), Colletotrichum orbiculare (C. orbiculare) and Alternaria alternata (A. alternata) were evaluated in vitro. The preliminary bioassays showed that some of the designed compounds displayed the promising antifungal activities against the above tested fungi. Strikingly, the target compounds 5f and 6h exhibited outstanding antifungal activity against B. cinerea at 100 μg/mL, with the corresponding inhibition rates reached 90.1 and 85.0%, which were better than the positive control Osthole (83.6%) and Azoxystrobin (46.5%). The compound 5f was identified as the promising fungicide candidate against B. cinerea with the EC50 values of 5.75 μg/mL, which was obviously better than Osthole (33.20 μg/mL) and Azoxystrobin (64.95 μg/mL). Meanwhile, the compound 5f showed remarkable antifungal activities against R. solani with the EC50 values of 28.96 μg/mL, which was better than Osthole (67.18 μg/mL) and equivalent to Azoxystrobin (21.34 μg/mL). The results provide a significant foundation for the search of novel fluorinated 7-hydroxycoumarin derivatives with good antifungal activity.
Design, synthesis and evaluation of wound healing activity for β-sitosterols derivatives as potent Na+/K+-ATPase inhibitors
Cui, Shaoyu,Jiang, Hongli,Chen, Lei,Xu, Jian,Sun, Wenzhuo,Sun, Haopeng,Xie, Zijian,Xu, Yunhui,Yang, Fubai,Liu, Wenyuan,Feng, Feng,Qu, Wei
, (2020/01/31)
β-Sitosterols, is a common steroid that can be identified in a variety of plants and their efficacy in promoting wound healing has been demonstrated. Na+/K+-ATPase, more than a pump, its signal transduction function for involvement in cell growth regulation attracts widespread concern. The Na+/K+-ATPase/Src receptor complex can serve as a receptor involved in multiple signaling pathways including promoting wound healing pathways. To finding potent accelerating wound healing small molecular, we choose the high inhibitory activity of Na+/K+-ATPase and non-cardiotoxic natural compound, β-sitosterol as the substrate. A series of β-sitosterol derivatives were designed, synthesized and evaluated as potential Na+/K+-ATPase inhibitors. Among them, compounds 31, 47, 49, showed improved inhibitory activity on Na+/K+-ATPase, with IC50 value of 3.0 μM, 3.4 μM, 2.2 μM, which are more potent than β-sitosterol with IC50 7.6 μM. Especially, compound 49 can induce cell proliferation, migration and soluble collagen production in L929 fibroblasts. Compared to model, compound 49 can accelerate wound healing in SD rats. Further studies indicated that 49 can activate the sarcoma (Src), uptake the protein kinase B (Akt), extracellular signal-regulated kinase (ERK) proteins expression in a concentration dependent manner. Finally, binding mode of compound 49 with Na+/K+-ATPase was studied, which provides insights into the determinants of potency and selectivity. These results proved β-stitosterol derivative 49 can serve as an effective inhibitor of Na+/K+-ATPase and potential candidate for accelerating wound healing agents.
Sterol derivatives and its preparation method and application
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Paragraph 0139-0141, (2019/05/19)
The invention discloses a sterol derivative of beta-sitosterol, beta-stigmasterol and cholesterol, and is shown as a formula VI. The invention also discloses a preparation method of the sterol derivative. The invention also discloses application of the sterol derivative to the aspect of preparation of wound healing promoting medicine. By starting from easily obtained natural products, the beta-sitosterol, the beta-stigmasterol and the cholesterol are used as starting raw materials; the synthetic method is simple; better operability and reaction yield are realized. The prepared sterol derivative has the obvious wound healing promoting activity; the multiplication, migration and collagen synthesis capability on L929 mechanocytes is obviously higher than that of the raw material and positive control medicine recombinant human bFGF (basic fibroblast growth factor). Compared with protide type medicine (such as bFGF), the prepared sterol derivative has more diversified dosage forms and medication modes; the reference is provided for the application in the field of wound healing promoting. The formula VI is shown as the accompanying diagram.
Compounds for inhibiting 1-deoxy-D-xylulose-5-phosphate reductoisomerase
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Page/Page column 41; 42; 43; 44, (2017/04/11)
In particular, the compound is effective to inhibit Dxr in Mycobacterium tuberculosis (Mtb). The present invention relates to compounds having general formula (I) or (II) where X is an acidic group, such as carboxylate, phosphonate, sulfate, and tetrazole; Ar is a substituted or unsubstituted aromatic or heteroaromatic group; and n is 0, 1, 2, 3, or 4, preferably 2, 3, or 4. The compounds inhibits 1-deoxy-D-xylulose-5-phosphate reductoisomerase (Dxr), particularly Dxr in Mycobacterium tuberculosis (Mtb).
Transformation of masked benzyl alcohols to: O -aminobenzaldehydes through C-H activation: A facile approach to quinazolines
Chen, Xiaolan,Han, Jian,Zhu, Yan,Yuan, Chunchen,Zhang, Jingyu,Zhao, Yingsheng
, p. 10241 - 10244 (2016/10/22)
Direct transformation of a directing group to important synthetic units would provide a high atom efficiency synthetic approach in synthetic chemistry. Herein, a convenient protocol for the synthesis of o-aminobenzaldehyde and benzoxazole derivatives from benzyl alcohols has been developed by employing (N,N-dimethyl)oxamoyl amide as a directing group in a palladium-catalyzed intramolecular amination. Furthermore, the attached directing center may not only be transformed into the product, but may also be further applied to generate synthetically important quinazoline and quinoline units. Finally, a high atom efficiency one-pot, two-step approach to form quinazolines from benzyl alcohol derivatives has been achieved in good yields, thus demonstrating its high utility.
Transition-Metal-Free Synthesis of N-Aryl Hydroxamic Acids via Insertion of Arynes
Zhang, Lanlan,Geng, Yu,Jin, Zhong
, p. 3542 - 3552 (2016/05/24)
An efficient and transition-metal-free N-arylation of amides via the insertion of arynes into the N-H bonds in the N-alkoxy amides is described. A variety of the reactive functional groups including the reactive aldehyde carbonyl group, furan ring, carbon-carbon double bonds, and free N-H bond of indole are found to be compatible with this process. In particular, the protocol is applicable in the synthesis of structurally diverse N-aryl hydroxamates and hydroxamic acids derived from N-protecting amino acids and peptides. In the presence of multiple amide N-H bonds, the N-arylation reaction can proceed selectively in the N-H bonds of terminal N-OBn amides giving rise to the desired N-aryl hydroxamates.
Synthesis of O-benzyl hydroxamates employing the sulfonate esters of N-hydroxybenzotriazole
Palakurthy, Nani Babu,Dev, Dharm,Paikaray, Sonali,Chaudhury, Susmitnarayan,Mandal, Bhubaneswar
, p. 7952 - 7958 (2014/02/14)
The direct conversion of various carboxylic acids, that include sterically hindered amino acids and di-peptides, to O-benzyl hydroxamates is demonstrated using sulfonate esters of benzotriazoles under ambient and milder conditions without significant race
Design of potential bisubstrate inhibitors against Mycobacterium tuberculosis (Mtb) 1-deoxy-d-xylulose 5-phosphate reductoisomerase (Dxr)-evidence of a novel binding mode
San Jose, Geraldine,Jackson, Emily R.,Uh, Eugene,Johny, Chinchu,Haymond, Amanda,Lundberg, Lindsay,Pinkham, Chelsea,Kehn-Hall, Kylene,Boshoff, Helena I.,Couch, Robin D.,Dowd, Cynthia S.
supporting information, p. 1099 - 1104 (2013/07/26)
In most bacteria, the nonmevalonate pathway is used to synthesize isoprene units. Dxr, the second step in the pathway, catalyzes the NADPH-dependent reductive isomerization of 1-deoxy-d-xylulose-5-phosphate (DXP) to 2-C-methyl-d-erythritol-4-phosphate (MEP). Dxr is inhibited by natural products fosmidomycin and FR900098, which bind in the DXP binding site. These compounds, while potent inhibitors of Dxr, lack whole cell activity against Mycobacterium tuberculosis (Mtb) due to their polarity. Our goal was to use the Mtb Dxr-fosmidomycin co-crystal structure to design bisubstrate ligands to bind to both the DXP and NADPH sites. Such compounds would be expected to demonstrate improved whole cell activity due to increased lipophilicity. Two series of compounds were designed and synthesized. Compounds from both series inhibited Mtb Dxr. The most potent compound (8) has an IC50 of 17.8 μM. Analysis shows 8 binds to Mtb Dxr via a novel, non-bisubstrate mechanism. Further, the diethyl ester of 8 inhibits Mtb growth making this class of compounds interesting lead molecules in the search for new antitubercular agents.
COMPOUNDS FOR INHIBITING 1- DEOXY-D-XYLULOSE- 5 - PHOSPHATE REDUCTOISOMERASE
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Paragraph 0065; 0066, (2013/03/26)
[0082] In particular, the compound is effective to inhibit Dxr in Mycobacterium tuberculosis (Mtb). The present invention relates to compounds having general formula (I) or where X is an acidic group, such as carboxylate, phosphonate, sulfate, and tetrazole; Ar is a substituted or unsubstituted aromatic or heteroaromatic group; and n is 0, 1, 2, 3, or 4, preferably 2, 3, or 4. The compounds inhibits l-deoxy-D-xylulose-5-phosphate reductoisomerase (Dxr), particularly Dxr in Mycobacterium tuberculosis (Mtb).
Synthesis of β- and γ-oxa isosteres of fosmidomycin and FR900098 as antimalarial candidates
Haemers, Timothy,Wiesner, Jochen,Giessmann, Dirk,Verbrugghen, Thomas,Hillaert, Ulrik,Ortmann, Regina,Jomaa, Hassan,Link, Andreas,Schlitzer, Martin,Van Calenbergh, Serge
, p. 3361 - 3371 (2008/09/20)
To expand the structure-activity relationships of fosmidomycin and FR900098, two potent antimalarials interfering with the MEP-pathway, we decided to replace a methylene group in β-position of the phosphonate moiety of these leads by an oxygen atom. β-oxa
