(-)-Cryptopleurine
(Synonyms: (R)-Cryptopleurine, NSC 19912) 目录号 : GC48635
An alkaloid with diverse biological activities
Cas No.:482-22-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(-)-Cryptopleurine is an alkaloid that has been found in Lauraceae and has diverse biological activities.1 It inhibits the growth of human A375 melanoma, A431 epidermoid carcinoma, A549 lung, MES-SA uterine sarcoma, and MCF-7 breast cancer cells (IC50 = 3 nM for all).2 (-)-Cryptopleurine inhibits hypoxia-induced gene expression in a hypoxia response element (HRE) reporter assay (IC50 = 8.7 nM).3 (-)-Cryptopleurine (500 µg/ml) prevents lesion formation in tobacco (N. tabacum) plants infected with tobacco mosaic virus (TMV).1 It also inhibits protein synthesis by yeast and mammalian ribosomes.4,5
1.Wang, Z., Feng, A., Cui, M., et al.First discovery and stucture-activity relationship study of phenanthroquinolizidines as novel antiviral agents against Tobacco Mosaic Virus (TMV)PLoS One7(12)e52933(2012) 2.Banwell, M.G., Bezos, A., Burns, C., et al.C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic propertiesBioorg. Med. Chem. Lett.16(1)181-185(2006) 3.Cai, X.F., Jin, X., Lee, D., et al.Phenanthroquinolizidine alkaloids from the roots of Boehmeria pannosa potently inhibit hypoxia-inducible factor-1 in AGS human gastric cancer cellsJ. Nat. Prod.69(7)1095-1097(2006) 4.Battaner, E., and Vazquez, D.Inhibitors of protein synthesis by ribosomes of the 80-S typeBiochim. Biophys. Acta254(2)316-330(1971) 5.Pestka, S., Rosenfeld, H., Harris, R., et al.Studies on transfer ribonucleic acid-ribosome complexes. XXI. Effect of antibiotics on peptidyl-puromycin synthesis by mammalian polyribosomesJ. Biol. Chem.247(21)6895-6900(1972)
| Cas No. | 482-22-4 | SDF | |
| 别名 | (R)-Cryptopleurine, NSC 19912 | ||
| Canonical SMILES | COC1=CC2=C3C(CN4[C@@](CCCC4)([H])C3)=C5C(C=C(C=C5)OC)=C2C=C1OC | ||
| 分子式 | C24H27NO3 | 分子量 | 377.5 |
| 溶解度 | 储存条件 | -20°C | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.649 mL | 13.245 mL | 26.4901 mL |
| 5 mM | 0.5298 mL | 2.649 mL | 5.298 mL |
| 10 mM | 0.2649 mL | 1.3245 mL | 2.649 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Total synthesis of (+)-antofine and (-)-Cryptopleurine
European J Org Chem 2013 May 1;2013(15):10.1002/ejoc.201300200.PMID:24357989DOI:10.1002/ejoc.201300200.
The tylophorine alkaloid anticancer compounds antofine and cryptopleurine have been synthesized in optically active form. Both syntheses employ optically pure α-amino acids as the starting materials, require only seven steps from known 2-ethynylpyrrolidine or 2-ethynylpiperidine derivatives, and are free of protecting groups. Key steps include an alkyne hydration and a chromium carbene complex based net [5+5]-cycloaddition step. Alkyne hydration was accompanied by racemization of the resulting β-aminoketone under most of the conditions examined, and successful minimization of this side reaction was achieved through careful pH control and choice of metal additive. Final ring closure involves a Bischler-Napieralski reaction using a carbamate (antofine) or urea (cryptopleurine) precursor.
Collective asymmetric synthesis of (-)-antofine, (-)-Cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine with tert-butanesulfinamide as a chiral auxiliary
J Org Chem 2014 Apr 18;79(8):3348-57.PMID:24679059DOI:10.1021/jo500013e.
A collective asymmetric synthesis of phenanthroindolizidine and phenanthroquinolizidine alkaloids (-)-antofine, (-)-Cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine was achieved by means of a reaction sequence involving efficient generation of chiral homoallylic amine intermediates by asymmetric allylation of the corresponding tert-butanesulfinyl imine. From these intermediates, the pyrrolidine and piperidine rings were constructed by means of an intramolecular SN2 substitution reaction and a ring-closing metathesis reaction, respectively. The unusual C5-methoxy-substituted phenanthrene moiety of (-)-tylocrebrine was generated by means of an InCl3-catalyzed cycloisomerization reaction of an o-propargylbiaryl compound.
Enantioselective approach to functionalized quinolizidines: synthesis of (+)-julandine and (+)-Cryptopleurine
Org Biomol Chem 2012 Sep 7;10(33):6776-84.PMID:22821193DOI:10.1039/c2ob25689d.
An efficient synthesis of functionalized quinolizidines was developed from an enantiomerically enriched γ-nitroketone, which is easily prepared by an organocatalytic ketone-nitroalkene Michael addition. Oxidative ring expansion of the nitroketone followed by reductive ring-opening leads to a suitably functionalized nitrodiol which is an intermediate to the title compounds.
Asymmetric synthesis of (R)-antofine and (R)-Cryptopleurine via proline-catalyzed sequential α-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehyde
J Org Chem 2010 Oct 15;75(20):7018-21.PMID:20843097DOI:10.1021/jo101510x.
Naturally occurring phenanthroindolizidine alkaloids (R)-antofine and phenanthroquinolizidine alkaloids (R)-Cryptopleurine have been synthesized in high optical purity via proline-catalyzed sequential α-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehyde. Both enantiopure forms of proline are commercially available, and thus, in principle, both isomers of antofine and cryptopleurine can be accessed with the new method.
Asymmetric total syntheses of (-)-antofine and (-)-Cryptopleurine using (R)-(E)-4-(tributylstannyl)but-3-en-2-ol
J Org Chem 2004 Apr 30;69(9):3144-9.PMID:15104454DOI:10.1021/jo049820a.
The asymmetric total syntheses of the representative phenanthroindolizidine and phenanthroquinolizidine alkaloids, (-)-antofine and (-)-Cryptopleurine, are described. An efficient synthetic pathway to the key intermediate 12, in enantiomerically pure form, was achieved by using a chiral building block (R)-9 and the Overman rearrangement with a total transfer of chirality. The problem of constructing the pyrrolidine and piperidine rings was successfully addressed, primarily by using a ring-closing metathesis reaction and a cross-metathesis reaction, respectively.