Herquline A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01718 |
| CAS | 71812-08-3 |
| Molecular Weight | 314.42 |
| Molecular Formula | C19H26N2O2 |
| Purity | ≥98% |
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Description
Herquline A is a new platelet aggregation inhibitor produced by Penicillium herquei Fg-372.
Specification
| Synonyms | Herqueline; Herquiline; 4H-5,2-(Iminomethano)-11,7-methenopyrrolo(3,2,1-no)(1)benzazacycloundecine-10,12-dione, 1,2,5,6,8,9,11,11a,13,14,14a,14b-dodecahydro-16-methyl-, (2R*,5R*,11S*,11aS*,14aS*,14bR*)-(-)- |
| Storage | Store at -20°C |
| IUPAC Name | (2S,3R,7R,8R,14S,17S)-15-methyl-1,15-diazapentacyclo[12.3.1.13,17.18,12.02,7]icos-12(20)-ene-6,9-dione |
| Canonical SMILES | CN1CC2CC3CCC(=O)C4C3N2CC1CC5=CC4C(=O)CC5 |
| InChI | InChI=1S/C19H26N2O2/c1-20-9-14-8-12-3-5-17(23)18-15-7-11(2-4-16(15)22)6-13(20)10-21(14)19(12)18/h7,12-15,18-19H,2-6,8-10H2,1H3/t12-,13+,14+,15+,18+,19+/m1/s1 |
| InChI Key | UFKNDVKQCSBIQE-OCANJJRCSA-N |
Properties
| Appearance | Crystal |
| Boiling Point | 499.5±45.0°C at 760 mmHg |
| Melting Point | 171-174°C (dec.) |
| Flash Point | 225.1±21.1 °C |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in DMSO, Methanol, Ethanol |
Reference Reading
1. Synthesis and Reactivity of 1-Hydroxyherquline A
Thomas T Kim, Sunkyu Han, Dongwook Kim, Hee-Seung Lee, Chungwoo Lee Org Lett . 2022 Mar 18;24(10):1964-1968. doi: 10.1021/acs.orglett.2c00379.
Herein, we present the synthesis of 1-hydroxyherquline A and describe its reactivity discovered during its attempted conversion to herquline A, a long-sought natural product target in the synthetic chemical community. The strategic installation of the C1 hydroxyl group enabled the keyaza-Michael addition-mediated N10-C2 bond formation and eventually access to 1-hydroxyherquline A, the most advanced herquline A congener reported to date. Our attempted reductive transformation of 1-hydroxyherquline A to herquline A was challenged by the extremely strained bowl-shaped pentacyclic structures of key precursors that prevented either radical formation at C1 or protonation (or hydrogenation) from the desired face. These discoveries regarding the innate chemical reactivities of advanced intermediates toward herquline A may prove useful in efforts toward this formidable target.
2. Herquline A, produced by Penicillium herquei FKI-7215, exhibits anti-influenza virus properties
Takuya Suga, Haruki Yamada, Kazuro Shiomi, Yukihiro Asami, Masato Iwatsuki, Fumitaka Momose, Takuya Chiba, Takayuki Nagai, Yoshihiro Watanabe, Kenichi Nonaka, Satoshi Ōmura Biosci Biotechnol Biochem . 2017 Jan;81(1):59-62. doi: 10.1080/09168451.2016.1162084.
In the course of screening for new anti-influenza virus antibiotics, we isolated herquline A from a culture broth of the fungus, Penicillium herquei FKI-7215. Herquline A inhibited replication of influenza virus A/PR/8/34 strain in a dose-dependent manner without exhibiting cytotoxicity against several human cell lines. It did not inhibit the viral neuraminidase.
3. Synthesis of Pentacyclic Framework of Herquline A
Sunkyu Han, Seongrok Heo, Thomas Taehyung Kim, Hee-Seung Lee, Chungwoo Lee Chem Asian J . 2021 Dec 1;16(23):3882-3885. doi: 10.1002/asia.202101004.
The highly strained bowl-shaped pentacyclic structure of herquline A has rendered it one of the most difficult problems in organic synthesis yet to be solved. The challenges associated with the synthesis of herquline A have been well documented in four Ph.D. dissertations and in multiple reports regarding syntheses of its structurally simpler congeners. Herein, we report the construction of the pentacyclic core of herquline A that contains both N10-C2 and C3-C3' bonds. The key for success was the development of the tandem aza-Michael addition/enolate capture protocol that set the stage for subsequent palladium catalyzed C3(sp2)-C3'(sp2) coupling reaction. Ensuing oxidative dearomatization of the left aryl ring allowed the formation of the pentacyclic diketone core of herquline A.
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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 ╳
