2-Propen-1-ol, 2-methyl-3-phenyl- - 1504-55-8

2-Propen-1-ol, 2-methyl-3-phenyl-

Catalog Number: EVT-288419
CAS Number: 1504-55-8
Molecular Formula: C10H12O
Molecular Weight: 148.2 g/mol
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Product Introduction

Description

The compound "2-Propen-1-ol, 2-methyl-3-phenyl-" is a structural motif present in various bioactive molecules and has been the subject of research due to its potential applications in medicinal chemistry and synthetic organic chemistry. The studies provided explore the synthesis, biological activity, and potential applications of compounds containing the phenylpropanol structure, which is closely related to "2-Propen-1-ol, 2-methyl-3-phenyl-".

Mechanism of Action

In the context of biological activity, the mechanism of action of these compounds varies depending on their structure and target. For instance, one study describes the synthesis of 1-phenyl-2-decanoylamino-3-morpholino-1-propanol, which is an inhibitor of glucosyltransferase involved in the formation of glucosylceramide, a key component in cell membranes. The active isomer of this compound was identified and characterized, showing uncompetitive inhibition against UDP-glucose and mixed competition against ceramide, with a Ki of 0.7 microM1. Another study synthesized a series of 3-(N-alkyl-N-phenylamino)propan-2-ol derivatives, which were evaluated as Src kinase inhibitors and showed anticancer activity on human breast carcinoma cells3. These studies highlight the diverse biological activities that can be modulated by phenylpropanol derivatives.

Applications in Various Fields

Medicinal Chemistry

The compounds synthesized in these studies have shown significant potential in medicinal chemistry. The active isomer of 1-phenyl-2-decanoylamino-3-morpholino-1-propanol could serve as a lead compound for the development of new treatments for diseases related to glucosylceramide metabolism, such as Gaucher's disease1. Similarly, the 3-(N-alkyl-N-phenylamino)propan-2-ol derivatives with Src kinase inhibitory activity could be further developed as anticancer agents, as demonstrated by their efficacy in inhibiting the growth of breast carcinoma cells3.

Synthetic Organic Chemistry

In synthetic organic chemistry, the versatility of phenylpropanol derivatives is evident. The study on 2-phenylthio-3-bromopropene showcases its utility as a synthon for annulation reactions and its conversion into other useful synthons, demonstrating the compound's role as a building block in complex organic synthesis2. This reagent could be used to construct a wide variety of chemical structures, which could have further applications in drug development and materials science.

Antimalarial Research

The antimalarial activity of related compounds, such as the series of 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl] [1,1'-biphenyl]-2-ols, indicates the potential of phenylpropanol derivatives in the development of new antimalarial drugs. These compounds showed excellent activity against resistant strains of Plasmodium berghei in mice and are promising candidates for clinical trials in humans4.

Properties

CAS Number

1504-55-8

Product Name

2-Propen-1-ol, 2-methyl-3-phenyl-

IUPAC Name

(E)-2-methyl-3-phenylprop-2-en-1-ol

Molecular Formula

C10H12O

Molecular Weight

148.2 g/mol

InChI

InChI=1S/C10H12O/c1-9(8-11)7-10-5-3-2-4-6-10/h2-7,11H,8H2,1H3/b9-7+

InChI Key

LLNAMUJRIZIXHF-VQHVLOKHSA-N

SMILES

CC(=CC1=CC=CC=C1)CO

Synonyms

(E)-2-methyl-3-phenyl-2-propen-1-ol
2-methyl-3-phenyl-2-propen-1-ol
2-methyl-3-phenyl-2-propen-1-ol, (E)-isomer
2-methyl-3-phenyl-2-propen-1-ol, (Z)-isome

Canonical SMILES

CC(=CC1=CC=CC=C1)CO

Isomeric SMILES

C/C(=C/C1=CC=CC=C1)/CO

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