L-783277
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02183 |
| CAS | 791807-02-8 |
| Molecular Weight | 364.39 |
| Molecular Formula | C19H24O7 |
| Purity | ≥95% |
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Description
L-783277 is originally isolated from Phoma sp.. It inhibits MEK2 with an IC50 of 4 nmol/L.
Specification
| Synonyms | (3S,5Z,8S,9S)-3,4,9,10,11,12-Hexahydro-8,9,16-trihydroxy-14-methoxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione; LL-783277 |
| Storage | Store at -20°C |
| IUPAC Name | (4S,6Z,9S,10S)-9,10,18-trihydroxy-16-methoxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),6,15,17-tetraene-2,8-dione |
| Canonical SMILES | CC1CC=CC(=O)C(C(CCCC2=C(C(=CC(=C2)OC)O)C(=O)O1)O)O |
| InChI | InChI=1S/C19H24O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3,7,9-11,15,18,21-23H,4-6,8H2,1-2H3/b7-3-/t11-,15-,18+/m0/s1 |
| InChI Key | QXPNJMHRUZCEAP-UXBSLASESA-N |
Reference Reading
1. Identification of a Unique Resorcylic Acid Lactone Derivative That Targets Both Lymphangiogenesis and Angiogenesis
Youngsun Han, Sandip Sengupta, Byung Joo Lee, Hanna Cho, Jiknyeo Kim, Hwan Geun Choi, Uttam Dash, Jin Hyoung Kim, Nam Doo Kim, Jeong Hun Kim, Taebo Sim J Med Chem. 2019 Oct 24;62(20):9141-9160. doi: 10.1021/acs.jmedchem.9b01025. Epub 2019 Oct 7.
We synthesized 11 novel L-783277 derivatives, in which a structure rigidifying phenyl ring is incorporated into the 14-membered chiral resorcylic acid lactone system. The SAR study with these substances demonstrated that 17 possesses excellent kinase selectivity against a panel of 335 kinases in contrast to L-783277 and inhibits VEGFR3, VEGFR2, and FLT3 with single-digit nanomolar IC50 values. Also, we found that 21, a stereoisomer of 17, has excellent potency (IC50 = 9 nM) against VEGFR3 and selectivity over VEGFR2 and FLT3. 17, a potent dual VEGFR3 and VEGFR2 inhibitor, effectively suppresses both lymphangiogenesis and angiogenesis in a 3D-microfluidic tumor lymphangiogenesis assay and in vivo corneal assay while SAR131675 blocks only lymphangiogenesis. In addition, 17 blocks the endothelial tube formation and suppresses proliferation of PHE tumor vascular model. 17 will be a valuable templatefor developing therapeutically active and selective substances that target both lymphangiogenesis and angiogenesis.
2. Natural and Synthetic Lactones Possessing Antitumor Activities
Younghoon Kim, Sandip Sengupta, Taebo Sim Int J Mol Sci. 2021 Jan 21;22(3):1052. doi: 10.3390/ijms22031052.
Cancer is one of the leading causes of death globally, accounting for an estimated 8 million deaths each year. As a result, there have been urgent unmet medical needs to discover novel oncology drugs. Natural and synthetic lactones have a broad spectrum of biological uses including anti-tumor, anti-helminthic, anti-microbial, and anti-inflammatory activities. Particularly, several natural and synthetic lactones have emerged as anti-cancer agents over the past decades. In this review, we address natural and synthetic lactones focusing on their anti-tumor activities and synthetic routes. Moreover, we aim to highlight our journey towards chemical modification and biological evaluation of a resorcylic acid lactone, L-783277 (4). We anticipate that utilization of the natural and synthetic lactones as novel scaffolds would benefit the process of oncology drug discovery campaigns based on natural products.
3. Asymmetric total syntheses of naturally occurring α,β-enone-containing RALs, L-783290 and L-783277 through intramolecular base-mediated macrolactonization reaction
Joy Chakraborty, Ankan Ghosh, Samik Nanda Org Biomol Chem. 2020 Mar 25;18(12):2331-2345. doi: 10.1039/d0ob00237b.
Asymmetric total synthesis of two naturally occurring α,β-enone containing RALs, L-783290 and L-783277 is described in this article. An E-selective Horner-Wadsworth-Emmons (HWE) olefination was used as a key reaction to construct the C7'-C8' olefinic unsaturation in L-783290. An enantiopure alkyne addition to the aldehyde followed by Z-selective partial reduction was employed to construct the C7'-C8' olefinic unsaturation in L-783277. Biomimetic lactonization reaction was used to construct the macrolactone core in both the target molecules.
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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 ╳
