3460-04-6

Basic information

• Product Name: 3-CHLORO-N-PHENYLPROPANAMIDE
• Synonyms: 3-CHLOROPROPIONANILIDE;3-CHLORO-N-PHENYLPROPANAMIDE;3-CHLORO-N-PHENYL-PROPIONAMIDE;3-Chloro-N-phenylpropionamide 3-Chloropropionanilide;Propanamide, 3-chloro-N-phenyl-
• CAS NO: 3460-04-6
• Molecular Formula: C₉H₁₀ClNO
• Molecular Weight: 183.63
• Mol File: 3460-04-6.mol

Chemical Properties

• Melting Point: 119.5-120.5 °C
• Boiling Point: 360.2 °C at 760 mmHg
• Flash Point: 171.7 °C
• Appearance: /
• Density: 1.22 g/cm³
• Vapor Pressure: 2.25E-05mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 14.20±0.70(Predicted)
• CAS DataBase Reference: 3-CHLORO-N-PHENYLPROPANAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-N-PHENYLPROPANAMIDE(3460-04-6)
• EPA Substance Registry System: 3-CHLORO-N-PHENYLPROPANAMIDE(3460-04-6)

Safety Data

• Hazardous Substances Data: 3460-04-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloro-N-phenylpropanamide is utilized as an intermediate in the synthesis of various drugs, playing a crucial role in the development of new pharmaceuticals. Its chemical structure allows for the creation of a diverse range of medicinal compounds, contributing to the advancement of treatments for various health conditions.
Used in Chemical Industry:
In the realm of organic synthesis, 3-Chloro-N-phenylpropanamide serves as a valuable reagent. Its unique properties enable it to participate in a variety of chemical reactions, facilitating the production of a wide array of organic compounds for various applications.
Used in Research and Development:
3-Chloro-N-phenylpropanamide's biological activity and potential therapeutic uses make it an important subject of study in research and development. Scientists and pharmaceutical chemists are interested in exploring its properties further to understand its full potential in the field of medicine and to develop new therapeutic agents based on its structure and activity.

InChI:InChI=1/C9H10ClNO/c10-7-6-9(12)11-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)

Upstream product

• 62-53-3 aniline 
• 625-36-5 2-chloropropionyl chloride 
• 19565-19-6 3-chloropropionylisothiocyanate 
• 802294-64-0 propionic acid 

Downstream Products

• 4734-37-6 N-phenyl-3-piperidin-1-yl-propionamide 
• 6634-43-1 3-carbamimidoylmercapto-propionic acid anilide; hydrochloride 
• 117023-92-4 4--N-phenyl-1-piperidinepropanamide 
• 126922-12-1 2-(4-Cyano-1-phenyl-6,7-dihydro-5H-[2]pyrindin-3-ylsulfanyl)-N-phenyl-acetamide 
• 5099-95-6 1-phenylazetidin-2-one 
• 2210-24-4 N-acryloylaniline 
• 4443-34-9 3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-N-phenylpropanamide 
• 90097-52-2 2-chloro-3-(chloropmethyl)quinoline 
• 895250-80-3 C₁₂H₁₃N₃O 
• 1125436-62-5 C₁₁H₁₂N₄O 
• 6833-29-0 N-phenyl pentanethioamide 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 13658-95-2 N¹,N¹-dimethyl-N³-phenylpropane-1,3-diamine 
• 106576-06-1 4-benzoyloxy-1-phenylazetidin-2-one 

Relevant articles and documents

Synthesis, in silico Study and Antileishmanial Evaluation of New Selenides Derived from 7-Chloro-quinoline and N-Phenylacetamides

This study describes a virtual screening performed for two series of selenides (28 compounds), derived from N-phenylacetamides chlorides and 7-chloro-quinoline, to determine their potential for leishmanicidal activity against Leishmania amazonensis and Leishmania donovani. Seven compounds were predicted as potential leishmanicides; therefore, they were synthesized from elemental selenium, as a precursor for the production of NaHSe, and subsequent reactions with 4,7-dichloro-quinoline and N-phenylacetamides chlorides were performed. The compounds were characterized by infrared (IR), 1H and 13C nuclear magnetic resonance (NMR), and sent for in vitro cytotoxicity tests against L. amazonensis and were found to be active and selective, and two compounds presented half-maximal inhibitory concentrations (IC50) of 5.67 and 10.81 μg mL-1. They also presented good interaction energies in the docking study, suggesting that may exert their effects by inhibiting the N-myristoyltransferase and O-acetylserine sulfhydrylase enzymes in parasites.

Tetrahydroquinoline-Capped Histone Deacetylase 6 Inhibitor SW-101 Ameliorates Pathological Phenotypes in a Charcot-Marie-Tooth Type 2A Mouse Model

Histone deacetylase 6 (HDAC6) is a promising therapeutic target for the treatment of neurodegenerative disorders. SW-100 (1a), a phenylhydroxamate-based HDAC6 inhibitor (HDAC6i) bearing a tetrahydroquinoline (THQ) capping group, is a highly potent and sel

Synthesis and Exploration of Abscisic Acid Receptor Agonists Against Dought Stress by Adding Constraint to a Tetrahydroquinoline-Based Lead Structure

New oxotetrahydroquinolinyl- and oxindolinyl sulfonamides interacting with RCAR/(PYR/PYL) receptor proteins were identified as lead structures against drought stress in crops starting from protein docking studies of a sulfonamide lead structure, followed by in-depth SAR studies. Optimized five to six step synthetic approaches via substituted amino oxo-tetrahydro-quinolines and amino oxo-indolines as essential intermediates gave access to the envisaged oxo-tetrahydroquinolinyl and oxindolinyl sulfonamides. Whilst oxo-tetrahydroquinolinyl sulfonamides with additional carbon substituents or spiro-cycloalkyl groups exhibited only low to moderate target affinities, the corresponding spiro-oxindolinyl and oxo-tetrahydroquinolinyl sulfonamides carrying optimized N-substituents revealed strong interactions with RCAR/(PYR/PYL) receptor proteins in Arabidopsis thaliana. Remarkably, the in vitro activity observed for these new compounds was on the same level as observed for the naturally occurring plant hormone in line with strong efficacy against drought stress in-vivo (canola and wheat as broad-acre crops).

Preparation method of 6-hydroxy-3,4-dihydro-2(1H)quinolinone

The invention belongs to the field of preparation of intermediates in chemical engineering, and particularly relates to a preparation method of 6-hydroxy-3,4-dihydro-2(1H)quinolinone. The preparationmethod comprises the following steps of using aniline and 3-chloropropionyl chloride as raw materials; performing cyclization, nitrification, reduction and diazotization hydrolysis, so as to synthesize the target product, namely 6-hydroxy-3,4-dihydro-2(1H)quinolinone. The preparation method has the advantages that the reaction conditions are mild, the cost is reduced, and the yield rate is increased.

Demonstration of in Vitro Resurrection of Aged Acetylcholinesterase after Exposure to Organophosphorus Chemical Nerve Agents

After the inhibition of acetylcholinesterase (AChE) by organophosphorus (OP) nerve agents, a dealkylation reaction of the phosphylated serine, referred to as aging, can occur. When aged, known reactivators of OP-inhibited AChE are no longer effective. Realkylation of aged AChE may provide a route to reversing aging. We designed and synthesized a library of quinone methide precursors (QMPs) as proposed realkylators of aged AChE. Our lead compound (C8) from an in vitro screen successfully resurrected 32.7 and 20.4% of the activity of methylphosphonate-aged and isopropyl phosphate-aged electric-eel AChE, respectively, after 4 days. C8 displays properties of both resurrection (recovery from the aged to the native state) and reactivation (recovery from the inhibited to the native state). Resurrection of methylphosphonate-aged AChE by C8 was significantly pH-dependent, recovering 21% of activity at 4 mM and pH 9 after only 1 day. C8 is also effective against isopropyl phosphate-aged human AChE.

Discovery of new potent protein arginine methyltransferase 5 (PRMT5) inhibitors by assembly of key pharmacophores from known inhibitors

Protein arginine methyltransferase 5 (PRMT5) is an epigenetics related enzyme that has been validated as a promising therapeutic target for human cancer. Up to now, two small molecule PRMT5 inhibitors has been put into phase I clinical trial. In the prese

Design of a Chemical Probe for the Bromodomain and Plant Homeodomain Finger-Containing (BRPF) Family of Proteins

The bromodomain and plant homeodomain finger-containing (BRPF) family are scaffolding proteins important for the recruitment of histone acetyltransferases of the MYST family to chromatin. Here, we describe NI-57 (16) as new pan-BRPF chemical probe of the bromodomain (BRD) of the BRPFs. Inhibitor 16 preferentially bound the BRD of BRPF1 and BRPF2 over BRPF3, whereas binding to BRD9 was weaker. Compound 16 has excellent selectivity over nonclass IV BRD proteins. Target engagement of BRPF1B and BRPF2 with 16 was demonstrated in nanoBRET and FRAP assays. The binding of 16 to BRPF1B was rationalized through an X-ray cocrystal structure determination, which showed a flipped binding orientation when compared to previous structures. We report studies that show 16 has functional activity in cellular assays by modulation of the phenotype at low micromolar concentrations in both cancer and inflammatory models. Pharmacokinetic data for 16 was generated in mouse with single dose administration showing favorable oral bioavailability.

Substituted indole compounds, as well as using method and application thereof

The invention relates to substituted indole compounds, a using method and application of the substituted indole compounds, as well as a medicine composition including the compounds and application thereof. The compounds or medicine composition can be used for inhibiting reuptake of 5-hydroxytryptamine. The invention further relates to a method for preparing the compounds and the medicine composition, as well as application of the compounds and medicine composition in treatment of central nervous system dysfunction.

Chemical exploration of 4-(4-fluorobenzyl)piperidine fragment for the development of new tyrosinase inhibitors

Tyrosinase is involved in the production of melanin through the hydroxylation of monophenols to o-diphenols. The role of this enzyme was extensively studied in order to identify new therapeutics preventing skin pigmentation and melanoma. In this work we initially identified the 3-(4-benzylpiperidin-1-yl)-1-(1H-indol-3-yl)propan-1-one (1a) as promising mushroom tyrosinase inhibitor (IC50= 252 μM). Then, several chemical modifications were performed and new analogues related to compound 1a were synthesized. Biochemical assays demonstrated that several obtained compounds proved to be effective inhibitors showing IC50values lower both than “lead compound” 1a and reference inhibitor kojic acid, as a well-known tyrosinase inhibitor. The inhibition kinetics analyzed by Lineweaver–Burk plots revealed that compounds 2 a-c and 10b act as non-competitive inhibitors while the most active inhibitor 2d (IC50= 7.56 μM) is a mixed-type inhibitor. Furthermore, experimental and computational structural studies were performed in order to clarify the binding mode of the derivative 2d.

Phenyl Benzenesulfonylhydrazides Exhibit Selective Indoleamine 2,3-Dioxygenase Inhibition with Potent in Vivo Pharmacodynamic Activity and Antitumor Efficacy

Tryptophan metabolism has been recognized as an important mechanism in immune tolerance. Indoleamine 2,3-dioxygenase plays a key role in local tryptophan metabolism via the kynurenine pathway and has emerged as a therapeutic target for cancer immunotherapy. Our prior study identified phenyl benzenesulfonyl hydrazide 2 as a potent in vitro (though not in vivo) inhibitor of indoleamine 2,3-dioxygenase. Further lead optimization to improve in vitro potencies and pharmacokinetic profiles resulted in N′-(4-bromophenyl)-2-oxo-2,3-dihydro-1H-indole-5-sulfonyl hydrazide 40, which demonstrated 59% oral bioavailability and 73% of tumor growth delay without apparent body weight loss in the murine CT26 syngeneic model, after oral administration of 400 mg/kg. Accordingly, 40, is proposed as a potential drug lead worthy of advanced preclinical evaluation.