52601-57-7

Basic information

• Product Name: (2E)-3-(1,3-benzodioxol-5-yl)-1-naphthalen-2-ylprop-2-en-1-one
• Synonyms: (2E)-3-(1,3-Benzodioxol-5-yl)-1-(2-naphthyl)prop-2-en-1-one; 2-propen-1-one, 3-(1,3-benzodioxol-5-yl)-1-(2-naphthalenyl)-, (2E)-
• CAS NO: 52601-57-7
• Molecular Formula: C₂₀H₁₄O₃
• Molecular Weight: 302.3234
• Mol File: 52601-57-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 498.6°C at 760 mmHg
• Flash Point: 247.7°C
• Density: 1.285g/cm³
• Vapor Pressure: 4.45E-10mmHg at 25°C
• Refractive Index: 1.702
• CAS DataBase Reference: (2E)-3-(1,3-benzodioxol-5-yl)-1-naphthalen-2-ylprop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-(1,3-benzodioxol-5-yl)-1-naphthalen-2-ylprop-2-en-1-one(52601-57-7)
• EPA Substance Registry System: (2E)-3-(1,3-benzodioxol-5-yl)-1-naphthalen-2-ylprop-2-en-1-one(52601-57-7)

Safety Data

• Hazardous Substances Data: 52601-57-7(Hazardous Substances Data)

Usage

Description

(2E)-3-(1,3-benzodioxol-5-yl)-1-naphthalen-2-ylprop-2-en-1-one, also known as "Nagelamide O," is a phenylpropene compound with a molecular formula of C24H16O3 and a molecular weight of 352.38 g/mol. It is a yellowish solid that has been identified as a natural product found in marine sponges. (2E)-3-(1,3-benzodioxol-5-yl)-1-naphthalen-2-ylprop-2-en-1-one exhibits various biological activities, such as antifungal and cytotoxic properties, and has a unique structure that makes it an interesting target for research in medicinal chemistry and drug development.

Uses

Used in Pharmaceutical Industry:
(2E)-3-(1,3-benzodioxol-5-yl)-1-naphthalen-2-ylprop-2-en-1-one is used as a pharmaceutical compound for its antifungal and cytotoxic properties. Its unique structure and potential pharmacological properties make it a promising candidate for the development of new drugs to treat various diseases.
Used in Medicinal Chemistry Research:
(2E)-3-(1,3-benzodioxol-5-yl)-1-naphthalen-2-ylprop-2-en-1-one is used as a research compound in medicinal chemistry to study its biological activities and explore its potential as a therapeutic agent. Its unique structure and natural occurrence in marine sponges provide valuable insights into the development of new drugs and understanding the mechanisms of action of this compound.

Upstream product

• 120-57-0 piperonal 
• 93-08-3 methyl 2-naphthyl ketone 
• 91-20-3 naphthalene 
• 75-36-5 acetyl chloride 

Downstream Products

• 1465270-14-7 C₂₃H₁₆O₂ 
• 1465270-32-9 C₃₀H₂₂O₄S 

Relevant articles and documents

A new series of thiazolyl pyrazoline derivatives linked to benzo[1,3]dioxole moiety: Synthesis and evaluation of antimicrobial and anti-proliferative activities

2-(5-(Benzo[d][1,3]dioxol-5-yl)-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-substituted phenyl)thiazole (7) and thiazole derivatives (9) were synthesized via reaction of 4,5-dihydro-1H-pyrazoles (5a,b) with substituted phenacyl bromide and a number of α-halo-compounds respectively. Also, (E)-2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(naphthalen-1-yl)-4,5 dihydro-1H-pyrazol-1-yl)-4-methyl-5-(substituted phenyldiazenyl)thiazole (11) were prepared through reactions of carbothioamide (5a,b) with hydrazonoyl halides. In addition, thioamides (5a–b) were used as starting materials for preparation of thiazoles (12a–b) and benzylidene thiazoles (13a–b). Most of synthesized compounds show interesting biological properties as antimicrobial and antiproliferative activities, the results of minimum inhibitory concentration showed that pyrazole derivative 7c (MIC: 0.23 mg/mL) showed better results when compared with 11c and 12a (MIC: 0.1–0.125 mg/mL) as obtained from their MIC values. On the other hand, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-chlorophenyl) thiazole (7c) can be considered as the most promising anti-proliferative agent against HCT-116 cancer cells owing to its notable inhibitory effect on HCT-116 cells with an IC50 value of 6.19 μM.

One-pot synthesis of multifunctionalized m-terphenyls

A facile one-step synthetic protocol toward multifunctionalized m-terphenyls 5 and sulfonyl m-terphenyls 6 is developed from substituted chalcones 1 and allyl sulfone 2 in good yields via a [3C+3C] annulation. The NaH-mediated annulation features transition metal catalyst-free condition. Chalcones 1 with the functional groups tolerance are easily prepared via Claisen-Schmidt condensation of substituted benzaldehydes 3 with acetophenone 4 in a qualitative yield under an aqueous alkaline methanolic solution.

Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones

Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. The cytotoxic potential of chalcones which consists of C6-C 3-C6 units gets enhanced by the incorporation of pyrazole ring as proved by our earlier studies. Thus in the present work, pyrazoles of chalcones with ring A substituted by furan, naphthalene and variety of substituted phenyl rings has been prepared and evaluated for in vitro cytotoxic activity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines. Springer Science+Business Media, LLC 2011.