Himbadine
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| Category | Others |
| Catalog number | BBF-04729 |
| CAS | 24932-15-8 |
| Molecular Weight | 329.48 |
| Molecular Formula | C21H31NO2 |
| Purity | >95% by HPLC |
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Description
Hibatidine is a piperidine alkaloid isolated from Galbulimima sp.
Specification
| Storage | Store at -20°C |
| IUPAC Name | (1R,2R,3R,8S,12S,13S,16R,18S)-12-hydroxy-16,17-dimethyl-17-azapentacyclo[10.7.1.02,11.03,8.013,18]icos-10-en-9-one |
| Canonical SMILES | CC1CCC2C(N1C)CC3CC2(C4=CC(=O)C5CCCCC5C34)O |
| InChI | InChI=1S/C21H31NO2/c1-12-7-8-16-18(22(12)2)9-13-11-21(16,24)17-10-19(23)14-5-3-4-6-15(14)20(13)17/h10,12-16,18,20,24H,3-9,11H2,1-2H3/t12-,13-,14+,15+,16+,18+,20-,21+/m1/s1 |
| InChI Key | ATJYANLRBFNIEG-FBMLLKETSA-N |
Properties
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Reference Reading
1. Enantioselective synthesis of a chiral intermediate of himbacine analogs by Burkholderia cepacia lipase A
Yanming Chen, Fei Gao, Guojun Zheng, Shuaihua Gao Biotechnol Lett. 2020 Dec;42(12):2643-2651. doi: 10.1007/s10529-020-02969-z. Epub 2020 Jul 20.
The enantiomers of (4R/S)-4-hydroxy-N, N-diphenyl-2-pentynamide are key chiral synthons for the synthesis of thrombin receptor antagonists such as vorapaxar. In this paper, we report the enzymatic preparation of enantiomerically enriched (4R)-4-hydroxy-N, N-diphenyl-2-pentynamide using lipase A from Burkholderia cepacia ATCC 25416 as the catalyst. First, the lipase gene (lipA) and its chaperone gene (lipB) was cloned and expressed in Escherichia coli system. After purification, lipase A activation was performed with the assistance of foldase lipase B. Enzyme assay revealed that the activated lipase A showed the optimal catalytic activity at 60 ºC and pH 7. The effects of various metals on the activity were investigated and results demonstrated that most of the metals inhibited the activity. To further improve the catalytic outcome, two-phase reaction was studied, and n-hexane proved to be a good organic solvent for the combination system. Using the optimize conditions, (4R)-4-hydroxy-N, N-diphenyl-2-pentynamide with 94.5% ee value and 48.93% conversion ratio was achieved. Our investigation on this lipase reveals lipase A as a promising biocatalyst for producing chiral propargyl alcohol for preparation of novel himbacine analogs.
2. Himbacine-derived thrombin receptor antagonists: c7-spirocyclic analogues of vorapaxar
Mariappan V Chelliah, Keith Eagen, Zhuyan Guo, Samuel Chackalamannil, Yan Xia, Hsingan Tsai, William J Greenlee, Ho-Sam Ahn, Stan Kurowski, George Boykow, Yunsheng Hsieh, Madhu Chintala ACS Med Chem Lett. 2014 Mar 11;5(5):561-5. doi: 10.1021/ml500008w. eCollection 2014 May 8.
We have synthesized several C7-spirocyclic analogues of vorapaxar and evaluated their in vitro activities against PAR-1 receptor. Some of these analogues showed activities and rat plasma levels comparable to vorapaxar. Compound 5c from this series showed excellent PAR-1 activity (K i = 5.1 nM). We also present a model of these spirocyclic compounds docked to the PAR-1 receptor based on the X-ray crystal structure of vorapaxar bound to PAR-1 receptor. This model explains some of the structure-activity relationships in this series.
3. Himbacine-derived thrombin receptor antagonists: c7-aminomethyl and c9a-hydroxy analogues of vorapaxar
Mariappan V Chelliah, Samuel Chackalamannil, Yan Xia, William J Greenlee, Ho-Sam Ahn, Stan Kurowski, George Boykow, Yunsheng Hsieh, Madhu Chintala ACS Med Chem Lett. 2013 Dec 18;5(2):183-7. doi: 10.1021/ml400452v. eCollection 2014 Feb 13.
We have synthesized several C7-aminomethyl analogues of vorapaxar that are potent PAR-1 antagonists. Many of these analogues showed excellent in vitro binding affinity and pharmacokinetics profile in rats. Compound 6a from this series showed excellent PAR-1 activity (K i = 5 nM). We have also synthesized a C9a-hydroxy analogue of vorapaxar, which showed very good PAR-1 affinity (K i = 19.5 nM) along with excellent rat pharmacokinetic profile and ex vivo efficacy in the cynomolgus monkey.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
