23173-26-4Relevant academic research and scientific papers
Studies in the eburnane series: A new dimerization process
Lewin, Guy,Schaeffer, Corinne
, p. 9689 - 9692 (1998)
The behaviour of the synthetic (-)-16-(aminomethyl)eburnamenine (prepared from apovincamine) with formaldehyde was studied. Carrying out the reaction in acetic acid led to an original dimer, while in trifluoroacetic acid a 12-functionalized eburnamonine was isolated.
Synthesis and biological evaluation of Vinpocetine derivatives
Pan, Bo-Wen,Shi, Yang,Li, Wen-Chao,Wang, Qing,Pan, Meng,Wu, Qiong,Fu, Hong-Zheng
, (2020)
A new series of Vinpocetine derivatives were synthesized and evaluated for their inhibitory activity on PDE1A in vitro. Seven compounds with higher inhibitory activity were selected for surface plasmon resonance (SPR) binding experiments. Compared with Vinpocetine, these high potency compounds presented a higher binding affinity with PDE1A, which was consistent with inhibitory activity. After further screening, compounds 5, 7, 21, 34 and Vinpocetine were selected to examine the vasorelaxant effects on endothelium-intact rat thoracic aortic rings. The study suggested that the effects of compounds 7 and 21 were the most significant with the maximum value of 93.46 ± 0.77% and 92.90 ± 0.78% (n = 5) at a concentration of 100 μM respectively. Based on these studies, compounds 7 and 21 were considered for further development as hit compounds.
Design, synthesis and biological evaluation of vincamine derivatives as potential pancreatic β-cells protective agents for the treatment of type 2 diabetes mellitus
Chen, Jing,Du, Te,Hu, Lihong,Liu, Xinpeng,Lv, Xue,Shen, Xu,Sun, Guanglong,Wang, Jiaying,Wang, Junwei,Xu, Jiawen
, (2020)
A series of vincamine derivatives were designed, synthesized and evaluated as pancreatic β-cells protective agents for type 2 diabetes mellitus. Most of the compounds displayed potent pancreatic β-cells protective activities and five derivatives were found to exhibit 20–50-fold higher activities than vincamine. Especially for compounds Vin-C01 and Vin-F03, exhibited a remarkable EC50 value of 0.22 μM and 0.27 μM, respectively. Their pancreatic β-cells protective activities increased approximately 2 times than vincamine. In cell viability assay, compounds Vin-C01 and Vin-F03 could effectively promote β-cell survival and protect β-cells from STZ-induced apoptosis. Further cellular mechanism of action studies demonstrated that their potent β-cells protective activities were achieved by regulating IRS2/PI3K/Akt signaling pathway. The present study evidently showed that compounds Vin-C01 and Vin-F03 were two more potent pancreatic β-cells protective agents compared to vincamine and might serve as promising lead candidates for the treatment of type 2 diabetes mellitus.
Pharmaceutical application of indole alkaloids and derivatives thereof
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Paragraph 0087-0090, (2020/06/17)
The invention discloses pharmaceutical application of indole alkaloids and derivatives thereof, belonging to the field of medicinal chemistry, pharmacology and preparations. The invention specificallyrelates to application of vinpocetine derivatives in treatment or prevention of diseases, cerebral arteriosclerosis, hypertension, hemorrhagic stroke sequelae, hyperviscosity and cerebral ischemia caused by ischemic cerebrovascular lesions, and application of the vinpocetine derivatives in preparation of a cerebrovascular dilator, a composition for improving ischemic cerebrovascular lesions and peripheral blood supply and a composition for improving the utilization rate of cerebral blood oxygen.
General and Phosphine-Free Cobalt-Catalyzed Hydrogenation of Esters to Alcohols
Shao, Zhihui,Zhong, Rui,Ferraccioli, Raffaella,Li, Yibiao,Liu, Qiang
supporting information, p. 1125 - 1130 (2019/10/22)
Catalytic hydrogenation of esters is essential for the sustainable production of alcohols in organic synthesis and chemical industry. Herein, we describe the first non-noble metal catalytic system that enables an efficient hydrogenation of non-activated esters to alcohols in the absence of phosphine ligands (with a maximum turnover number of 2391). The general applicability of this protocol was demonstrated by the high-yielding hydrogenation of 39 ester substrates including aromatic/aliphatic esters, lactones, polyesters and various pharmaceutical molecules.
Pervone derivative and purpose thereof to treatment of diabetes B
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, (2018/03/28)
The invention relates to the field of medicinal chemistry, in particular to a derivative shown as a general formula (I) and a purpose of a medicine composition containing the derivative to preparationof medicine for treating diabetes B. The compound has the effect of preventing pancreatic island beta cell apoptosis and can be used for treating the diabetes B. The general formula (I) is shown in the description.
DIAZA-BENZOFLUORANTHRENE COMPOUNDS
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Paragraph 0090; 0091; 0092, (2018/02/27)
Disclosed are a series of diaza-benzofluoranthrene compounds. The present invention particularly relates to a compound represented by formula (I), pharmaceutically acceptable salts or tautomers thereof.
Synthesis of azecino[5,4-b]indoles and indolo[3,2-e][2]benzazonines via tandem transformation of hydrogenated indoloquinolizines and indolizines
Voskressensky,Borisova,Titov,Listratova,Kulikova,Varlamov,Khrustalev,Aleksandrov
, p. 1231 - 1241 (2013/07/26)
The reactions of partially hydrogenated indole-fused quinolizines and indolizines with activated alkynes in methanol, acetonitrile, and dichloromethane were studied. The reactions were shown to be accompanied by the cleavage of the bridging C-N bond. Azec
Asymmetric Total Synthesis of (+)-Apovincamine and a Formal Synthesis of (+)-Vincamine. Demonstration of a Practical "Asymmetric Linkage" between Aromatic Carboxylic Acids and Chiral Acyclic Substrates
Schultz, Arthur G.,Malachowski, William P.,Pan, You
, p. 1223 - 1229 (2007/10/03)
Asymmetric syntheses of (+)-apovincamine (la) and (+)-vincamine (2) are described. Construction of the pentacyclic diene lactam 14, a pivotal intermediate for synthesis of the cis-fused vincane-type alkaloids, began by Birch reduction - alkylation of the chiral benzamide 3 to give the 6-ethyl-l-methoxy-4-methyl-l,4-cyclohexadiene 4. Conversion of 4 to 2,5-cyclohexadienone 5 (92percent overall yield from 3) and HPLC analysis of 5 demonstrated the diastereomeric purity resulting from the Birch reduction - alkylation to be > 100:1. Dienone 5 was converted to butyrolactone 9 (47percent overall yield from 3), and 9 was coupled with tryptamine (10) to give the amide lia. Amido keto aldehyde 13 was obtained from 11a, and acid-catalyzed tricyclization and subsequent base-induced elimination of MeOH provided the desired cis-fused pentacyclic diene lactam 14. Examination of the two-step process 13 -14 revealed a novel base-induced epimerization at C(21) which served to interconvert 14 and 17, possibly by the involvement of a homoenolate. Diene lactam 14 was converted to (+)-apovincaminal 20a, an intermediate in the synthesis of (+)-apovincamine (la) reported by Winterfeldt and co-workers. A new procedure for conversion of 20a to la involves conversion of 20a to the acetal 20b and treatment of 20b with NBS/AIBN in CCl4. The conversion of la to vincamine (2) has been reported by Oppolzer and co-workers.
