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654280

Sigma-Aldrich

1-(Phenylsulfonyl)-3-indolylboronic acid pinacol ester

97%

Synonym(s):

1-(Phenylsulfonyl)-3-indoleboronic acid pinacol ester

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About This Item

Empirical Formula (Hill Notation):
C20H22BNO4S
CAS Number:
870717-93-4
Molecular Weight:
383.27
MDL number:
MFCD08276778
UNSPSC Code:
12352103
PubChem Substance ID:
24884024
NACRES:
NA.22

Quality Level

100

assay

97%

form

solid

mp

120-125 °C

SMILES string

CC1(C)OB(OC1(C)C)c2cn(c3ccccc23)S(=O)(=O)c4ccccc4

InChI

1S/C20H22BNO4S/c1-19(2)20(3,4)26-21(25-19)17-14-22(18-13-9-8-12-16(17)18)27(23,24)15-10-6-5-7-11-15/h5-14H,1-4H3

InChI key

OMZLHWZHHPAZPW-UHFFFAOYSA-N

Related Categories

Application

1-(Phenylsulfonyl)-3-indolylboronic acid pinacol ester can be used:
  • In one or two key synthetic steps for the preparation of a key intermediate of lycogarubin C.
  • To prepare 3-(4,5-dibromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-1-(phenylsulfonyl)-1H-indole, a key intermediate for the synthesis of tubulin inhibitor VERU-111 analogs.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SHBK2061
SHBC7528V
SHBC7521V
27397MJV
27397MJ

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Qinghui Wang et al.
Journal of medicinal chemistry, 61(17), 7877-7891 (2018-08-21)
Colchicine binding site inhibitors (CBSIs) hold great potential in developing new generations of antimitotic drugs. Unlike existing tubulin inhibitors such as paclitaxel, they are generally much less susceptible to resistance caused by the overexpression of drug efflux pumps. The 3,4,5-trimethoxyphenyl
John T Gupton et al.
Tetrahedron, 70(52), 9759-9767 (2015-01-15)
Lycogarubin C, permethyl storniamide A and lamellarin G trimethyl ether are pyrrole containing, natural products, which exhibit interesting biological properties. Such properties include anti-tumor activity on a variety of cancer cell lines including those that confer drug resistance, inhibition of

Articles

Boronic Acid Esters

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