65329-03-5Relevant academic research and scientific papers
Tanshinol and H2 S/NO Donor binding, preparation method thereof and application in pharmacy (by machine translation)
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Paragraph 0080-0082, (2020/08/18)
The invention belongs to the field of chemical pharmacy, and relates to active ingredient tanshinol and H in Chinese herbal medicine Salvia miltiorrhiza. 2 S/NO Donors and its preparation method and use in pharmacy, especially in the preparation of medicines for preventing and treating cardiovascular and cerebrovascular diseases and inflammation related diseases. To the invention, through in-vitro oxidative stress injury and inflammation model experiments, the results show that H is obviously inhibited. 2 O2 In vivo activity experiment results show that the conjugate is capable of remarkably inhibiting the release of inflammatory cytokines induced by LPS (LPS), reducing inflammation-induced mouse peritoneal macrophages, obviously inhibiting the release of inflammatory cytokines induced by LPS, and showing the result that the compound can be used for preparing drugs for preventing and treating cardiovascular and cerebrovascular diseases and inflammatory diseases. (by machine translation)
Deracemization and Stereoinversion of α-Amino Acids by l-Amino Acid Deaminase
Rosini, Elena,Melis, Roberta,Molla, Gianluca,Tessaro, Davide,Pollegioni, Loredano
, p. 3773 - 3781 (2017/11/13)
Enantiomerically pure α-amino acids are compounds of primary interest for the fine chemical, pharmaceutical, and agrochemical sectors. Amino acid oxidases are used for resolving d,l-amino acids in biocatalysis. We recently demonstrated that l-amino acid deaminase from Proteus myxofaciens (PmaLAAD) shows peculiar features for biotechnological applications, such as a high production level as soluble protein in Escherichia coli and a stable binding with the flavin cofactor. Since l-amino acid deaminases are membrane-bound enzymes, previous applications were mainly based on the use of cell-based methods. Now, taking advantage of the broad substrate specificity of PmaLAAD, a number of natural and synthetic l-amino acids were fully converted by the purified enzyme into the corresponding α-keto acids: the fastest conversion was obtained for 4-nitrophenylalanine. Analogously, starting from racemic solutions, the full resolution (ee >99%) was also achieved. Notably, d,l-1-naphthylalanine was resolved either into the d- or the l-enantiomer by using PmaLAAD or the d-amino acid oxidase variant having a glycine at position 213, respectively, and was fully deracemized when the two enzymes were used jointly. Moreover, the complete stereoinversion of l-4-nitrophenylalanine was achieved using PmaLAAD and a small molar excess of borane tert-butylamine complex. Taken together, recombinant PmaLAAD represents an l-specific amino acid deaminase suitable for producing the pure enantiomers of several natural and synthetic amino acids or the corresponding keto acids, compounds of biotechnological or pharmaceutical relevance. (Figure presented.).
Improved process for pilot-scale synthesis of danshensu ((±)-DSS) and its enantiomer derivatives
Bai, Yajun,Zhang, Qunzheng,Jia, Pu,Yang, Lingjian,Sun, Yuhong,Nan, Yefei,Wang, Shixiang,Meng, Xue,Wu, Yizhen,Qin, Fanggang,Sun, Zhe,Gao, Xiaokang,Liu, Pei,Luo, Kai,Zhang, Yajun,Zhao, Xinfeng,Xiao, Chaoni,Liao, Sha,Liu, Jianli,Wang, Cuiling,Fang, Jiacheng,Wang, Xiaoxiao,Wang, Jing,Gao, Rong,An, Xuexia,Zhang, Xunli,Zheng, Xiaohui
, p. 1667 - 1673 (2015/02/18)
A pilot-scale process has been developed for green and scalable synthesis of (±)-β-(3,4-dihydroxyphenyl) lactic acid ((±)-DSS) and their two important derivatives, namely, (±)-IDHP [(±)-isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate] and (±)-DBZ [(±)-bornyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate]. Subsequent hydrogenation has been carried out by employing Raney Ni as catalyst. The improved process results in higher yields of 47.5% for (±)-DBZ and 49.2% for (±)-IDHP compared to the initial process with a yield of 12% for (±)-DBZ and 18% for (±)-IDHP in our original medicinal chemistry route. Furthermore, kilograms of optical DBZ [(-)-S-DBZ and (+)-R-DBZ, >99% ee] and IDHP [(-)-S-IDHP and (+)-R-IDHP, >99% ee] have been produced by chiral high-performance liquid chromatography in good yield (>84%).
Green synthesis of β-(3,4-dihydroxyphenyl)lactic acid
Zhang, Qun-Zheng,Wang, Yi,Nan, Ye-Fei,Xiong, Xun-Yu,Pan, Qing,Zhang, Xun-Li
, p. 7158 - 7160 (2013/08/23)
A new method has been developed for the synthesis of β-(3,4- dihydroxyphenyl)lactic acid, an active ingredient for the treatment of myocardial ischemia. Pd/C catalysts were used in the key reduction reaction to replace the traditionally used toxic Zn/Hg catalysts. A significantly high product yield of 99.7 % was obtained under the optimal reaction conditions, through the use of orthogonal experimental design, when reaction temperature, catalyst (5 % Pd/C) amount and pressure were 60 °C, 20 wt % and 1.0 MPa, respectively.
The synthesis and biological evaluation of novel Danshensu-cysteine analog conjugates as cardiovascular-protective agents
Jia, Yaoling,Zhou, Pengfei,Wang, Yang,Dong, Xiaoyi,Liu, Xinhua,Pan, Lilong,Xin, Hong,Zhu, Yi Zhun
, p. 176 - 187,12 (2020/07/31)
A series of novel amide and thioester conjugates between Danshensu and cysteine derivatives have been designed and synthesized based on the strategy of "medicinal chemical hybridization". Pharmacological evaluation indicated that the amide conjugates 3a/4a/17a and thioester conjugates 6a-d exhibited obvious protective effects on H2O2-induced human umbilical vein endothelial cells (HUVECs). Pretreated with these conjugates could increase glutathione (GSH) activity and decrease malondialdehyde (MDA) level. Further study on mechanism of compound 4a revealed that it was related to its mitochondrial-protective effect and regulation of apoptosis-related proteins expression (Bax, p53, PARP, caspase-3, caspase-9 and Bcl-2). These results indicate that these Danshensu-cysteine analog conjugates possess significant cardiovascular-protective effects and merit further investigation.
SUBSTITUTED BETA-PHENYL-ALPHA-HYDROXY PROPANOIC ACID, SYNTHESIS METHOD AND USE THEREOF
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Page/Page column 6, (2009/02/10)
The present invention relates to a compound of the formula (I), wherein R1, R2 and R3 are each independently selected from H, OH, F, Cl, Br, methoxy and ethoxy; or alternatively, R1 and R2 together form -OCH2O-, R3 is selected from H, OH, methoxy, ethoxy and halogens; R4 is OH or acyloxy; R5 is cycloalkoxyl, amino and substituted amino, and when R5 is selected from amino, at least one of R1, R2 and R3 is not H. The present invention further relates to a process for synthesizing a compound of the formula (I), and use of the compound of the formula (I) in the manufacture of a medicament for the prevention or treatment of cardiovascular or cerebrovascular diseases.
Asymmetric synthesis and biological evaluation of Danshensu derivatives as anti-myocardial ischemia drug candidates
Dong, Cunnan,Wang, Yang,Zhu, Yi Zhun
experimental part, p. 3499 - 3507 (2009/09/08)
The synthesis and bioactivities of Danshensu derivatives (R)-methyl 2-acetoxy-3-(3,4-diacetoxyphenyl)propanoate (1a), (R)-methyl 2-acetoxy-3-(3,4-methylenedioxyphenyl)propanoate (1b) and their racemates 7 and 10 were reported in this paper. These derivati
A modified synthesis of (±)-β-aryllactic acids
Wong,Xu,Chang,Lee
, p. 793 - 797 (2007/10/02)
The synthesis of racemic forms of the reportedly active principle of Danshen, namely (±)-β-(3,4-dihydroxyphenyl)lactic acid [(±)3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid] and its seven racemic derivatives is reported.
