312734-34-2

Basic information

• Product Name: N-(2-FLUORO-PHENYL)-3,4-DIMETHOXY-BENZAMIDE
• Synonyms: N-(2-FLUORO-PHENYL)-3,4-DIMETHOXY-BENZAMIDE
• CAS NO: 312734-34-2
• Molecular Formula: C₁₅H₁₄FNO₃
• Molecular Weight: 275.2749632
• Mol File: 312734-34-2.mol

Chemical Properties

• Boiling Point: 333.0±42.0 °C(Predicted)
• Appearance: /
• Density: 1.248±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 12.10±0.70(Predicted)
• CAS DataBase Reference: N-(2-FLUORO-PHENYL)-3,4-DIMETHOXY-BENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-FLUORO-PHENYL)-3,4-DIMETHOXY-BENZAMIDE(312734-34-2)
• EPA Substance Registry System: N-(2-FLUORO-PHENYL)-3,4-DIMETHOXY-BENZAMIDE(312734-34-2)

Safety Data

• Hazardous Substances Data: 312734-34-2(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
N-(2-FLUORO-PHENYL)-3,4-DIMETHOXY-BENZAMIDE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a promising candidate in the development of new drugs with specific therapeutic targets.
Used in Pharmaceutical Research:
In pharmaceutical research, N-(2-FLUORO-PHENYL)-3,4-DIMETHOXY-BENZAMIDE is utilized for investigating its potential biological activities. N-(2-FLUORO-PHENYL)-3,4-DIMETHOXY-BENZAMIDE's structural elements, including the fluorine substitution and methoxy groups, may contribute to its interaction with biological targets, making it a valuable tool for studying molecular mechanisms and developing therapeutic agents.
Used in Drug Design and Development:
N-(2-FLUORO-PHENYL)-3,4-DIMETHOXY-BENZAMIDE is employed as a lead compound in drug design and development processes. Its structural features can be optimized and modified to enhance its pharmacological properties, potentially leading to the creation of novel and effective medications for various diseases and conditions.
Used in Biochemical Studies:
N-(2-FLUORO-PHENYL)-3,4-DIMETHOXY-BENZAMIDE is also used in biochemical studies to understand its interactions with enzymes, receptors, or other biological molecules. Such studies can provide insights into the compound's mechanism of action and its potential use in treating specific medical conditions.

Upstream product

• 348-54-9 2-Fluoroaniline 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 

Downstream Products

• 872726-54-0 4-fluoro-2-(3,4-dimethoxyphenyl)benzothiazole 
• 872726-67-5 N-(2-fluorophenyl)-3,4-dimethoxybenzothioamide 

Relevant articles and documents

Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer

Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.

Synthesis of carbon-11 labeled fluorinated 2-arylbenzothiazoles as novel potential PET cancer imaging agents

Fluorinated 2-arylbenzothiazoles are new potential antitumor drugs, which show potent and selective inhibitory activity against breast, lung, and colon cancer cell lines. Carbon-11 labeled fluorinated 2-arylbenzothiazoles may serve as novel probes for positron emission tomography (PET) to image tyrosine kinase in cancers. The preparation of 4-fluorinated 2-arylbenzothiazoles 4-fluoro-2-(3-benzloxy-4-methoxyphenyl)benzothiazole (6a) and 4-fluoro-2-(3,4-dimethoxyphenyl)benzothiazole (6b) was achieved by a modification of Jacobson thioanilide radical cyclization chemistry. Hydrogenolytic cleavage of the benzyl ether group of compound 6a using H2/Pd-C provided the precursor 4-fluoro-2-(3-hydroxy-4-methoxyphenyl)benzothiazole (7) for radiolabeling. Synthesis of radiolabeling precursors and the reference standards 5- and 6-fluorinated arylbenzothiazoles (11c-n) was achieved via the reaction of o-aminothiophenol disulfides with substituted benzaldehydes under reducing conditions. The target radiotracers carbon-11 labeled 4-, 5-, and 6-fluorinated arylbenzothiazoles (3-[11C]6b, 4-[11C]11c, 3-[11C]11c, 5-[11C]11f, 4-[11C]11f, 4-[11C]11i, 3-[11C]11i, 5-[11C]11l, and 4-[11C]11l) were prepared by O-[11C]methylation of the phenolic hydroxyl precursors (7, 11d, 11e, 11g, 11h, 11j, 11k, 11m, and 11n) with [11C]methyl triflate and isolated by solid-phase extraction (SPE) purification in 30-55% radiochemical yields.

Antitumor benzothiazoles. 26.1 2-(3,4-dimethoxyphenyl)-5- fluorobenzothiazole (GW 610, NSC 721648), a simple fluorinated 2-arylbenzothiazole, shows potent and selective inhibitory activity against lung, colon, and breast cancer cell lines

A series of new 2-phenylbenzothiazoles has been synthesized on the basis of the discovery of the potent and selective in vitro antitumor properties of 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (8n; GW 610, NSC 721648). Synthesis of analogues substituted in the benzothiazole ring was achieved via the reaction of o-aminothiophenol disulfides with substituted benzaldehydes under reducing conditions. Compounds were evaluated in vitro in four human cancer cell lines, and compound 8n was found to possess exquisitely potent antiproliferative activity (GI50 0.1 nM for MCF-7 and MDA 468). Potent and selective activity was also observed in the NCI 60 human cancer cell line panel. Structure-activity relationships established that the compound 8n stands on a pinnacle of potent activity, with most structural variations having a deactivating in vitro effect. Mechanistically, this new series of agents contrasts with the previously reported 2-(4-aminophenyl)benzothiazoles; compound 8n is not reliant on induction of CYP1A1 expression for antitumor activity.