15196-83-5

Usage

Uses

Used in Pharmaceutical Industry:
5-Chlorosalicylic Acid Ethyl Ester is used as an intermediate for the preparation of quinoline derivatives, which are known to act as TGFβ inhibitors. These inhibitors are essential in the development of drugs targeting various diseases and conditions, particularly those related to cell growth and proliferation.
As a result, 5-Chlorosalicylic Acid Ethyl Ester plays a crucial role in the synthesis of compounds that can potentially be used in the treatment of cancer and other TGFβ-related disorders. Its ability to be used as an intermediate in the preparation of quinoline derivatives highlights its importance in the pharmaceutical industry and its contribution to the development of novel therapeutic agents.

InChI:InChI=1/C9H9ClO3/c1-2-13-9(12)7-5-6(10)3-4-8(7)11/h3-5,11H,2H2,1H3

Upstream product

• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 7664-93-9 sulfuric acid 
• 321-14-2 5-chloro-2-hydroxybenzoic acid 
• 1128-76-3 3-chloro-benzoic acid ethyl ester 
• 64-17-5 ethanol 

Downstream Products

• 5022-48-0 5-chlorosalicylhydrazide 
• 159323-96-3 ethyl 5-chloro-2-hydroxy-3-nitrobenzoate 
• 73050-77-8 chloro-5 α,α-diethyl hydroxy-2 benzene methanol 
• 81028-88-8 3-(2-carboxy-4-chlorophenoxy)thiophene 
• 115438-07-8 5-Chloro-2-sulfamoyloxy-benzoic acid ethyl ester 
• 88599-38-6 2-Carbamoyloxy-5-chloro-benzoic acid ethyl ester 
• 38524-72-0 5-Chloro-2-(ethoxy-propylsulfanyl-phosphoryloxy)-benzoic acid ethyl ester 
• 57202-99-0 (2-carbethoxy-4-chlorophenoxy)-acetic acid ethyl ester 
• 68215-73-6 2-(4-amino-6-morpholin-4-ylamino-[1,3,5]triazin-2-yl)-4-chloro-phenol 
• 73119-79-6 ethyl 5-chloro-2-ethoxybenzoic acid 
• 7120-43-6 5-chlorosalicylamide 
• 62871-12-9 5-chloro-2-ethoxybenzoic acid 

Relevant academic research and scientific papers

Discovery of Isatin-Based Carbohydrazones as Potential Dual Inhibitors of Fatty Acid Amide Hydrolase and Monoacylglycerol Lipase

Using ligand-based design strategy, a set of isatin-3-carbohydrazones was designed, synthesized and evaluated for dual fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL) inhibition properties. Compound 5-chloro-N′-(5-chloro-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 b) emerged as a potent MAGL inhibitor with nanomolar activity (IC50=3.33 nM), while compound 5-chloro-N′-(1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 j) was the most potent selective FAAH inhibitor (IC50=37 nM). Compound 5-chloro-N′-(6-chloro-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 c) showed dual FAAH-MAGL inhibitory activity with an IC50 of 31 and 29 nM respectively. Enzyme kinetics studies revealed that the isatin-based carbohydrazones are reversible inhibitors for both FAAH and MAGL. Further, blood-brain permeability assay confirmed that the lead compounds (13 b, 13 c, 13 g, 13 m and 13 q) are suitable as CNS candidates. Molecular dynamics simulation studies revealed the putative binding modes and key interactions of lead inhibitors within the enzyme active sites. The lead dual FAAH-MAGL inhibitor 13 c showed significant antioxidant activity and neuroprotection in the cell-based cytotoxicity assay. In summary, the study yielded three potent FAAH/MAGL inhibitor compounds (13 b, 13 c and 13 j) with acceptable pharmacokinetic profile and thus can be considered as promising candidates for treating neurological and mood disorders.

Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids

We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.

Ruthenium(II)-catalyzed synthesis of hydroxylated arenes with ester as an effective directing group

An unprecedented Ru(II) catalyzed ortho-hydroxylation has been developed for the facile synthesis of a variety of multifunctionalized arenes from easily accessible ethyl benzoates with ester as an efficient directing group. Both the TFA/TFAA cosolvent system and oxidants serve as the critical success factors in this transformation. The reaction demonstrates excellent reactivity, good functional group tolerance, and high yields.

Synthesis, antibacterial activity, and quantitative structure-activity relationships of new (Z)-2-(nitroimidazolylmethylene)-3(2 H)-benzofuranone derivatives

A new series of (Z)-2-(1-methyl-5-nitroimidazole-2-ylmethylene)-3(2 H)-benzofuranones (11a-p) and (Z)-2-(1-methyl-4-nitroimidazole-5-ylmethylene)-3(2 H)-benzofuranones (12a-m) were synthesized and assayed for their antibacterial activity against Gram-positive and Gram-negative bacteria. Most of the 5-nitroimidazole analogues (11a-p) showed a remarkable inhibition of a wide spectrum of Gram-positive bacteria (Staphylococcus aureus, Streptococcus epidermidis, MRSA, and Bacillus subtilis) and Gram-negative Klebsiella pneumoniae, whereas 4-nitroimidazole analogues (12a-m) were not effective against selected bacteria. The quantitative structure-activity relationship investigations were applied to find out the correlation between the experimentally evaluated activities with various parameters of the compounds studied. The QSAR models built in this work had reasonable predictive power and could be explained by the observed trends in activities.

BENZOXAZOLE DERIVATIVES AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT

A compound represented by the following general formula (1) : wherein R1 represents a halogen atom, R2 represents hydrogen atom or a lower alkyl group, and R3 represents hydrogen atom, a lower alkyl group, a lower alkoxyl group, a hydroxy lower alkyl group, a halogen atom, or a substituted or unsubstituted amino group, wherein a substituent on the amino group is selected from the group consisting of a lower alkyl group, a lower alkenyl group, a lower alkylcarbonyl group, and an amino protective group, or a salt thereof. The compound of the present invention or a salt thereof is useful as an active ingredient of medicaments for preventive and/or therapeutic treatment of conditions of irritable bowel syndrome and digestive tract functional disorder, or condition of diarrhea.

Isoxazole derivatives

An isoxazole compound having the following formula: wherein R1 represents hydrogen, halogen, alkyl, alkoxy, hydroxyl, alkylthio, amino, alkanoyl, alkanoylamino, alkanoyloxy, alkoxycarbonyl, carboxy, (alkylthio)thiocarbonyl, carbamoyl, nitro or cyano; R2 represents an amino; m is 1; n is 1 to 6; ring A represents a phenyl ring or a naphthyl ring; and X represents oxygen or sulfur. The isoxazole compound has an excellent monoamine oxidase inhibitory activity, and is useful for treating Parkinson's disease, depression and Alzheimer's disease.