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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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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

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