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Wang H.,Southwest University | Yan J.-F.,Chengdu DiAo Pharmaceutical Group Co. | Song X.-L.,Southwest University | Fan L.,Southwest University | And 4 more authors.
Bioorganic and Medicinal Chemistry | Year: 2012

We wish to report the further design and improved synthesis that resulted in two series of target molecules, TM-1 and TM-2, with remarkably simplified structures containing β-amino ketone of discrete nabumetone moiety. These were obtained via a 'one-pot, two-step, three-component' protocol of Mannich reaction with yield up to 97%. A total of 28 out of 31 new compounds were characterized using 1H NMR, 13C NMR, ESI MS and HRMS techniques. Studies on their antidiabetic activities, screened in vitro at 10 μg mL -1 level, indicate that TM-2 possesses peroxisome proliferator-activated receptor activation and α-glucosidase inhibition activity significantly stronger than that of TM-1, and also that of the series B compounds that were previously synthesized by the group. Analysis of the structure-activity relationship points to the sulfanilamide unit as the most probable potent group of β-amino ketone and, on the basis of which, a tangible strategy is presented for the development of new antidiabetic drugs. © 2011 Elsevier Ltd. All rights reserved.


Yang Y.,Southwest University | Yan J.-F.,Chengdu DiAo Pharmaceutical Group Co. | Fan L.,Southwest University | Chen X.,Chengdu DiAo Pharmaceutical Group Co. | And 2 more authors.
Yaoxue Xuebao | Year: 2012

The discovery of high performance leading antidiabetic compounds containing sulfonamide and 4-aminophenylacetic acid moieties is reported. This was achieved by the synthesis of 6 intermediates and subsequently 20 target molecules using 4-aminophenylacetic acid as the starting materials, and through a few synthetic routes aided by multi-step reactions including sulfonylation of amino group, deacylation of amides and esterification of carboxyl group, as well as acylation of amino group. The chemical structures of the twenty-four new compounds were determined using 1H NMR, 13C NMR and HR-MS techniques. Screening in vitro of their peroxisome proliferator-activated receptor (PPAR) activation activities showed weak relative PPAR activation activities to most of the target molecules. However, 4 target molecules exhibit PPAR over 58%, and as high as 81.79% for TM2-i, presenting itself as potent leading compound for antidiabetic drugs. This research also confirms that it is probable to achieve esterification of carboxyl group and deacylation of fatty acid N-phenyl amides concurrently in SOCl2/alcohol solvent system. This provides new synthetic method for the selective reaction within molecules containing both carboxyl and N-aryl amido groups of fatty acids.


Tang G.,Southwest University | Yan J.,Chengdu di Ao Pharmaceutical Group Co. | Fan L.,Southwest University | Xu J.,Southwest University | And 4 more authors.
Science China Chemistry | Year: 2013

The synthesis of two series of β-amino ketones containing a p-aminobenzoic acid moiety (TM-1 and TM-2) using a modified protocol of the Mannich reaction is reported. The molecular structures of a total of tweenty three new target compounds were characterized by 1H NMR, 13C NMR, ESI-MS and HR-MS. Subsequently, their antidiabetic activities were screened in vitro. The α-glucodase inhibition (α-GI) activity of compound 1e reached a remarkable level of 66.50%. The peroxisome proliferator-activated receptor (PPAR) relative activation activities of six compounds are above 80%, and in particular 2i displays an unprecedentedly high PPAR of 130.91%. The structure-activity relationships of the compounds were established. 2i is also subject to further in-depth investigation. © 2013 Science China Press and Springer-Verlag Berlin Heidelberg.


Li M.-S.,CAS Chengdu Institute of Organic Chemistry | Li M.-S.,University of Chinese Academy of Sciences | Zhang Q.,CAS Chengdu Institute of Biology | Hu D.-Y.,CAS Chengdu Institute of Organic Chemistry | And 6 more authors.
Tetrahedron Letters | Year: 2016

A simple and catalyst-free method has been developed for the construction of β-hydroxyphosphine oxides through direct difunctionalization of alkenes with H-phosphine oxides and dioxygen under mild conditions. Preliminary mechanistic studies indicated that the hydroxyl oxygen atom of β-hydroxyphosphine oxide originated from the dioxygen and the present reaction might involve a radical process. © 2016 Elsevier Ltd.


Yang D.-C.,Southwest University | Yan J.-F.,Chengdu di Ao Pharmaceutical Group Co. | Xu J.,Southwest University | Ye F.,Chengdu di Ao Pharmaceutical Group Co. | And 4 more authors.
Yaoxue Xuebao | Year: 2010

Searching for new antidiabetic lead compound, 4-(1-aryl-3-oxo-5- phenylpentylamino) benzene-sulfonamides were designed and synthesized directly by three component one-pot condensation of 4-phenyl-2-butanone and sulfanilamide with some aromatic aldehydes at an yield of 23%-97%. The chemical structures of the twelve new Mannich bases were confirmed by 1H NMR, 13C NMR, FTIR, ESI-MS and HR-MS. The screening results of antidiabetic activity indicated that most of these title compounds possess α-glucosidase inhibitory activity, among which compound 1e is the strongest one. And compound 1l possesses good peroxisome proliferator-activated receptor response element (PPRE) agonist activity. The structure-activity relationship of these new β-amino ketones containing benzenesulfonamide unit was also discussed preliminarily.


Zhang K.,Southwest University | Yan J.-F.,Chengdu di Ao Pharmaceutical Group Co. | Tang X.-M.,Southwest University | Liu H.-P.,Southwest University | And 3 more authors.
Yaoxue Xuebao | Year: 2011

Twenty five new β-aminoalcohols containing nabumetone moiety were prepared via the reduction of potassium borohydride with a convenient and efficient procedure, starting from β-aminoketones that have been synthesized by our group. Their chemical structures were determined by IR, MS, 1H NMR, 13C NMR, HR-MS and antidiabetic activities were screened in vitro. Preliminary results revealed that the antidiabetic activity of most β-aminoalcohols were better than that of the corresponding β-aminoketones. Although most compounds showed weak antidiabetic activity, the α-glucosidase inhibitory activity of compounds 5hd1 and 5id2 reached 74.37% and 90.15%, respectively, which were superior to the positive control. The relative peroxisome proliferator-activated receptor response element (PPRE) activity of five compounds were more than 60%, among them compound 5ca possessed the highest activity (112.59%). As lead molecules of antidiabetic agents, compounds 5hd1, 5id2 and 5ca deserve further study.


Trademark
Chengdu Diao Pharmaceutical Group Co. | Date: 2011-02-14

Medicines for the treatment of cardiovascular diseases; Medicinal drinks; Food for babies; Air purifying preparations; Dietetic foods, namely, crackers adapted for medical use; Pesticides; Cotton for medical purposes; Dental lacquer.


Patent
Chengdu Diao Pharmaceutical Group Co. | Date: 2015-08-13

Disclosed are a phthalic hydrazide (phthalazine ketone) compound, and a pharmaceutical composition comprising the same. As a DNA repair enzyme poly (ADP-ribozyme) polymerase inhibitor, the compound and the pharmaceutical composition can effectively treat diseases involving PARP enzymatic activity, including cancer, neural degenerative diseases, inflammation and the like.


Patent
Chengdu Diao Pharmaceutical Group Co. | Date: 2014-11-05

Disclosed are a phthalic hydrazide (phthalazine ketone) compound, and a pharmaceutical composition comprising the same. As a DNA repair enzyme poly (ADP-ribozyme) polymerase inhibitor, the compound and the pharmaceutical composition can effectively treat diseases involving PARP enzymatic activity, including cancer, neural degenerative diseases, inflammation and the like.


Patent
Chengdu Diao Pharmaceutical Group Co. | Date: 2012-12-03

Disclosed are a phthalic hydrazide (phthalazine ketone) compound, and a pharmaceutical composition comprising the same. As a DNA repair enzyme poly (ADP-ribozyme) polymerase inhibitor, the compound and the pharmaceutical composition can effectively treat diseases involving PARP enzymatic activity, including cancer, neural degenerative diseases, inflammation and the like.

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