structure of (1-(tert-Butoxycarbonyl)-4-methoxy-1H-indol-2-yl)boronic acid

(1-(tert-Butoxycarbonyl)-4-methoxy-1H-indol-2-yl)boronic acid

CAS No.: 1000068-23-4
M. Wt: 291.10700
M. Fa: C14H18BNO5
InChI Key: BEXQWPHMBFKSLF-UHFFFAOYSA-N
Appearance: Pale-yellow Solid

Names and Identifiers of 1000068-23-4

CAS Number

1000068-23-4

EC Number

689-211-2

MDL Number

MFCD11616286

IUPAC Name

[4-methoxy-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic acid

InChI

InChI=1S/C14H18BNO5/c1-14(2,3)21-13(17)16-10-6-5-7-11(20-4)9(10)8-12(16)15(18)19/h5-8,18-19H,1-4H3

InChIKey

BEXQWPHMBFKSLF-UHFFFAOYSA-N

Canonical SMILES

B(C1=CC2=C(N1C(=O)OC(C)(C)C)C=CC=C2OC)(O)O

UNSPSC Code

12352100

Physical and chemical properties of 1000068-23-4

Exact Mass

291.12800

H Bond Acceptors

4

H Bond Donors

2

LogP

1.11290

Molecular Formula

C14H18BNO5

Molecular Weight

291.10700

PSA

80.92000

Storage condition

2-8°C

Safety Information of 1000068-23-4

Pictograms

Signal Word

Warning

Safety Data Sheet

Supports customized editing of SDS information and downloading in PDF documents.

Applications of 1000068-23-4

(1-(tert-Butoxycarbonyl)-4-methoxy-1H-indol-2-yl)boronic acid has several potential applications:

  • Drug Development: Its ability to interact with biological targets makes it suitable for developing new therapeutic agents, especially in oncology and metabolic disorders.
  • Chemical Biology: The compound can serve as a tool for studying enzyme mechanisms and interactions due to its reversible binding properties with diols.
  • Synthetic Chemistry: It is useful in organic synthesis as a building block for creating more complex molecules through cross-coupling reactions.

Interaction Studies of 1000068-23-4

Interaction studies involving (1-(tert-Butoxycarbonyl)-4-methoxy-1H-indol-2-yl)boronic acid typically focus on its binding affinity towards specific enzymes or receptors. These studies often employ techniques such as:

  • Surface Plasmon Resonance: To measure real-time binding interactions between the compound and target proteins.
  • Isothermal Titration Calorimetry: To determine thermodynamic parameters associated with binding events.
  • Molecular Docking Studies: Computational approaches are used to predict how (1-(tert-Butoxycarbonyl)-4-methoxy-1H-indol-2-yl)boronic acid interacts at the molecular level with various biological targets.

Biological Activity of 1000068-23-4

The biological activity of (1-(tert-Butoxycarbonyl)-4-methoxy-1H-indol-2-yl)boronic acid is primarily attributed to its indole structure and boronic acid functionality. Research indicates that compounds containing indole moieties exhibit a range of pharmacological effects, including anti-cancer, anti-inflammatory, and antimicrobial activities.

The boronic acid part allows for interactions with enzymes such as serine proteases and glycosidases, potentially leading to inhibition or modulation of their activities. This makes it a candidate for further exploration in drug discovery, particularly against diseases where these enzymes play critical roles.

Physical sample testing spectrum (NMR) of 1000068-23-4

Physical sample testing spectrum (NMR) of 1000068-23-4

Retrosynthesis analysis of 1000068-23-4

  • Route#1

    Cas:1093759-59-1
    Cas:5419-55-6
    Cas:1000068-23-4
  • Route#2

    Cas:1093759-59-1
    Cas:1000068-23-4