Thailanstatin A

Thailanstatin A 구조식 이미지
카스 번호:
1426953-21-0
상품명:
Thailanstatin A
동의어(영문):
Thailanstatin A;Terance Statin A;Thailandstatin A;6-dioxaspiro[2.5]oct-5-yl]acetic acid;ADC Payload,natural,Inhibitor,inhibit,SF3b,subunit,antiproliferative,Thailanstatin A,spliceosome,ADC,ADC Cytotoxin,RNA,linker;2-[(3R,5S,7R,8R)-7-[(1E,3E)-5-[(2S,3S,5R,6R)-5-[(2Z,4S)-4-(acetyloxy)pent-2-enamido]-3,6-dimethyloxan-2-yl]-3-methylpenta-1,3-dien-1-yl]-8-hydroxy-1,6-dioxaspiro[2.5]octan-5-yl]acetic acid;1,6-Dioxaspiro[2.5]octane-5-acetic acid, 7-[(1E,3E)-5-[(2S,3S,5R,6R)-5-[[(2Z,4S)-4-(acetyloxy)-1-oxo-2-penten-1-yl]amino]tetrahydro-3,6-dimethyl-2H-pyran-2-yl]-3-methyl-1,3-pentadien-1-yl]-8-hydroxy-, (3R,5S,7R,8R)-
CBNumber:
CB08099484
분자식:
C28H41NO9
포뮬러 무게:
535.63
MOL 파일:
1426953-21-0.mol

Thailanstatin A 속성

끓는 점
757.3±60.0 °C(Predicted)
밀도
1.23±0.1 g/cm3(Predicted)
용해도
DMSO : 250 mg/mL (466.74 mM; Need ultrasonic)
산도 계수 (pKa)
4.37±0.10(Predicted)
물리적 상태
Solid
색상
White to off-white
InChIKey
GJKQDOMCDFJANR-FUDLAKRJSA-N
SMILES
O1[C@@]2([C@H](O)[C@@H](/C=C/C(/C)=C/C[C@@H]3O[C@H](C)[C@H](NC(=O)/C=C\[C@@H](OC(C)=O)C)C[C@@H]3C)O[C@H](CC(O)=O)C2)C1

안전

Thailanstatin A C화학적 특성, 용도, 생산

개요

Thailanstatin A, a promising lead compound for drug discovery and development efforts, is derived from Thailandensis burkholderia MSMB43. It reveals low nanomolar to subnanomolar cytotoxicity against a variety of human cancer cell lines.

Mechanism of action

The mechanism of action (MOA) of thailanstatin A is the inhibition of spliceosome assembly. Thailanstatin A binds firmly to the SF3b subunit of the U2 snRNA sub-complex, a crucial component of the spliceosome. Since the spliceosomes of cancer cells are more active and exhibits higher mutation rates than those of normal cells, this sub-cellular component is by far the most well-established anti-tumor target in novel drug discoveries.

Synthesis

Synthesis_1426953-21-0
Thailanstatin A (1): To a stirred solution of epoxide 6 (4.0 mg, 0.012 mmol, 1.0 equiv) and boronate 5 (5.8 mg, 13 |ìmol, 1.1 equiv) in rigorously degassed (freeze-pump-thaw technique3) 3:1:1 1,4-dioxane/MeCN/H2O (0.64 mL,) at 25C. was added tripotassium phosphate monohydrate (2.8 mg, 0.012 mmol, 1.0 equiv) followed by Pd(dppf)Cl2.CH2Cl2 (0.1 mg, 0.125 |ìmol, 0.025 equiv). After 10 min, the reaction mixture was neutralized with phosphate buffer (NaH2PO4, 1.0 M, 2.5 mL), filtered through a layer of Celite, and rinsed thoroughly with ethyl acetate (20 mL). Then the organic layer was dried with anhydrous sodium sulfate and concentrated in vacuo. The obtained residue was purified by reversed-phase HPLC (C18, |19150 mm, Atlantis, 40ú50% aqueous MeCN containing 0.03% TFA) to afford thailanstatin A (1) (ca. 3.0 mg, 6.0 |ìmol, 52%) as a white foam.

Thailanstatin A 준비 용품 및 원자재

원자재

준비 용품


Thailanstatin A 공급 업체

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