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244056-94-8

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  • (2R,3R)-rel-3-Hydroxy-2-(2-propenyl)-1-piperidinecarboxylic Acid Phenylmethyl Ester

    Cas No: 244056-94-8

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244056-94-8 Usage

Chemical Properties

Colourless Oil

Check Digit Verification of cas no

The CAS Registry Mumber 244056-94-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,4,4,0,5 and 6 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 244056-94:
(8*2)+(7*4)+(6*4)+(5*0)+(4*5)+(3*6)+(2*9)+(1*4)=128
128 % 10 = 8
So 244056-94-8 is a valid CAS Registry Number.
InChI:InChI=1/C16H21NO3/c1-2-7-14-15(18)10-6-11-17(14)16(19)20-12-13-8-4-3-5-9-13/h2-5,8-9,14-15,18H,1,6-7,10-12H2/t14-,15-/m0/s1

244056-94-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name benzyl (2S,3S)-3-hydroxy-2-prop-2-enylpiperidine-1-carboxylate

1.2 Other means of identification

Product number -
Other names (2S*,3S*)-BENZYL 2-ALLYL-3-HYDROXY-1-PIPERIDINECARBOXYLATE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:244056-94-8 SDS

244056-94-8Relevant articles and documents

Synthesis and biological evaluation of isofebrifugine analogues

Zhang, Jinjin,Huang, Baohua,Lu, Yujing,Li, Wenbin,Zhuang, Zichong,Ke, Donghua,Zhong, Jingpeng,Zhou, Jinlin,Chen, Qian

, p. 1004 - 1010 (2019/11/22)

Isofebrifugine, as a kind of natural quinazolinone alkaloid with important physiological activities and good pharmacological effects, was isolated from a Chinese medicinal plant, Chang Shan (Dichroa febrifuga). In this paper, the synthesis of a series of novel isofebrifugine analogues was accomplished by employing the N-alkylation of 4(3H)-quinazolinones with benzyl (3aR,7aR)-rel-2-(bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)carboxylates and the subsequent N-deprotection. These analogues were characterized by1 H NMR,13 C NMR and HRMS spectra. The MTT assay was used to examine the inhibitory effects of these analogues on the growth of human hepatoma cells (HepG2). The results indicated that some halogenated or hemiketal analogues showed interesting inhibition activity.

BF3·Et2O catalyzed diastereoselective nucleophilic reactions of 3-silyloxypiperidine N,O-acetal with silyl enol ether and application to the asymmetric synthesis of (+)-febrifugine

Liu, Ru-Cheng,Huang, Wei,Ma, Jing-Yi,Wei, Bang-Guo,Lin, Guo-Qiang

scheme or table, p. 4046 - 4049 (2009/10/11)

The asymmetric BF3·Et2O catalyzed nucleophilic reactions of 3-silyloxypiperidine N,O-acetal 10 with silyl enol ethers derived from ketones are described. (+)-Febrifugine 1, an antimalarial alkaloid, was successfully synthesized based

Metabolites of febrifugine and its synthetic analogue by mouse liver S9 and their antimalarial activity against Plasmodium malaria parasite

Hirai, Shingo,Kikuchi, Haruhisa,Kim, Hye-Sook,Begum, Khurshida,Wataya, Yusuke,Tasaka, Hidehisa,Miyazawa, Yuriko,Yamamoto, Keisuke,Oshima, Yoshiteru

, p. 4351 - 4359 (2007/10/03)

Quinazolinone type alkaloids, febrifugine (1) and isofebrifugine (2), isolated from Dichroa febrifuga roots, show powerful antimalarial activity against Plasmodium falciparum. Unfortunately, their emetic effect and other undesirable side effects have precluded their clinical use for malaria. Because of their antimalarial potency, analogues were searched for, with the goal of preserving the strong antimalarial activity, while dramatically reducing side effects. We expected that compounds useful in drug development would exist in metabolites derived from 1 and Df-1 (3), the condensation product of 1 with acetone, by mouse liver S9. Feb-A and -B (4 and 5) were isolated as the major metabolites of 1. In addition to 4 and 5, feb-C and -D (6 and 7) were also purified from the metabolic mixture of 3. Compounds 4 and 5 were compounds oxidized at C-6 and C-2 of the quinazolinone ring of 1, respectively. Compounds 6 and 7, derived from 3, also bear febrifugine type structures in which the 4″- and 6″-positions of the piperidine ring of 1 were oxidized. In vitro antimalarial and cytotoxic tests using synthetically obtained racemic 4-6 and enantiomerically pure 7 demonstrated that 4 and 6 had antimalarial activity against P. falciparum, of similar potency to that of 1, with high selectivity. The antimalarial activity of 5 and 7, however, was dramatically decreased in the test. The in vitro antimalarial activity of analogues 22 and 43, which are stereoisomers of 4 and 6, was also evaluated, showing that 22 is active. The results suggest that basicity of both the 1- and the 1″-nitrogen atoms of 1 is crucial in conferring powerful antimalarial activity. Racemic 4 and 6 exhibited powerful in vivo antimalarial activity against mouse malaria P. berghei, and especially, no serious side effects were observed with 4. Thus, the metabolite 4 appears to be a promising lead compound for the development of new types of antimalarial drugs.

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