Drimentine A
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| Category | Antibiotics |
| Catalog number | BBF-04227 |
| CAS | 204398-90-3 |
| Molecular Weight | 503.72 |
| Molecular Formula | C32H45N3O2 |
| Purity | >98% by HPLC |
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Description
It is produced by the strain of Actinomycete strain MST-8651. It belongs to a novel class of antibiotics, possessing a new terpenylated diketopiperazine structure, with antibacterial, antifungal and anthelmintic activity.
Specification
| Synonyms | (3S,5aS,10bS,11aS)-10b-[[(1S,4aS,8aS)-Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methyl]-6,10b,11,11a-tetrahydro-3-(2-methylpropyl)-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione; [3S-[3α,5aα,10bα(1R*,4aR*,8aR*),11aβ]]-10b-[(Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl)methyl]-6,10b,11,11a-tetrahydro-3-(2-methylpropyl)-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione |
| Storage | Store at -20°C |
| IUPAC Name | (1S,4S,7S,9S)-9-[[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione |
| Canonical SMILES | CC(C)CC1C(=O)N2C(CC3(C2NC4=CC=CC=C43)CC5C(=C)CCC6C5(CCCC6(C)C)C)C(=O)N1 |
| InChI | InChI=1S/C32H45N3O2/c1-19(2)16-24-28(37)35-25(27(36)33-24)18-32(21-10-7-8-11-23(21)34-29(32)35)17-22-20(3)12-13-26-30(4,5)14-9-15-31(22,26)6/h7-8,10-11,19,22,24-26,29,34H,3,9,12-18H2,1-2,4-6H3,(H,33,36)/t22-,24-,25-,26-,29-,31+,32-/m0/s1 |
| InChI Key | DXEZZWASEJCIRP-ANXNZIBUSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Crystal |
| Antibiotic Activity Spectrum | Fungi; Parasites; Bacterial |
| Boiling Point | 671.1±55.0°C at 760 mmHg |
| Melting Point | 130-132°C |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO, Chloroform |
Reference Reading
1. Polycyclic hybrid isoprenoids from a reed rhizosphere soil derived Streptomyces sp. CHQ-64
Tianjiao Zhu, Qianqun Gu, Qian Che, Jing Li, Dehai Li, Robert A Keyzers, Xiaofang Liu J Nat Prod . 2013 Apr 26;76(4):759-63. doi: 10.1021/np3008864.
Two new hybrid isoprenoids, named indotertine B (2) and drimentine H (3), along with the known analogue drimentine C (4), were isolated from the reed rhizosphere soil derived actinomycete Streptomyces sp. CHQ-64. The structures of these compounds, including absolute configurations, were elucidated by extensive NMR, MS, and CD analyses. Indotertine B (2) exists as a pair of rotamers about the N-C(O) bond with a 2:1 ratio and displays activities against HCT-8 and A549 tumor cell lines with IC50 values of 6.96 and 4.88 μM, respectively.
2. Studies towards the total synthesis of drimentine C. Preparation of the AB and CDEF ring fragments
Christopher J Douglas, Sarah M Pound, Steven J Underwood European J Org Chem . 2020 May 3;2020(16):2448-2453. doi: 10.1002/ejoc.202000158.
The drimentine family is a class of hybrid isoprenoids derived fromactinomycetebacteria. Members of this family display weak antitumor and antibacterial activity. Herein we report our efforts toward the total synthesis of drimentine C using three distinct approaches incorporating palladium-catalyzed cyanoamidation, reductive cross-coupling, and photoredox-catalyzed α-alkylation of an aldehyde as key steps. Our synthetic efforts use a convergent synthesis to assemble the terpenoid and alkaloid portions of drimentine C from readily available l-tryptophan, l-proline, and (+)-sclareolide.
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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 ╳
