5022-48-0

Basic information

• Product Name: 5-CHLORO-2-HYDROXY-BENZOIC ACID HYDRAZIDE
• Synonyms: AKOS B015013;5-CHLORO-2-HYDROXYBENZOHYDRAZIDE;5-CHLORO-2-HYDROXY-BENZOIC ACID HYDRAZIDE;ART-CHEM-BB B015013;CHEMBRDG-BB 3015013;5-chloro-2-hydroxybenzohydrazide(SALTDATA: FREE)
• CAS NO: 5022-48-0
• Molecular Formula: C₇H₇ClN₂O₂
• Molecular Weight: 186.6
• Product Categories: Phenyls & Phenyl-Het
• Mol File: 5022-48-0.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Density: 1.465g/cm³
• Refractive Index: 1.634
• CAS DataBase Reference: 5-CHLORO-2-HYDROXY-BENZOIC ACID HYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-2-HYDROXY-BENZOIC ACID HYDRAZIDE(5022-48-0)
• EPA Substance Registry System: 5-CHLORO-2-HYDROXY-BENZOIC ACID HYDRAZIDE(5022-48-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 5022-48-0(Hazardous Substances Data)

Usage

Description

5-CHLORO-2-HYDROXY-BENZOIC ACID HYDRAZIDE is a versatile chemical compound characterized by the presence of a chlorine atom, a benzene ring, and a hydrazide functional group. It serves as a key building block in the synthesis of various products, including pharmaceuticals, agrochemicals, and dyes, due to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
5-CHLORO-2-HYDROXY-BENZOIC ACID HYDRAZIDE is used as a synthetic intermediate for the development of new pharmaceuticals. Its ability to form various chemical bonds and its reactivity make it a valuable component in the creation of novel drug molecules with potential therapeutic applications.
Used in Agrochemical Industry:
5-CHLORO-2-HYDROXY-BENZOIC ACID HYDRAZIDE is used as an active ingredient in the production of herbicides and fungicides. Its anti-bacterial and anti-fungal properties enable it to effectively control the growth of unwanted microorganisms and pests, thereby protecting crops and enhancing agricultural productivity.
Used in Dye and Pigment Industry:
5-CHLORO-2-HYDROXY-BENZOIC ACID HYDRAZIDE is used as a key component in the synthesis of dyes and pigments for the textile industry. Its ability to form stable color compounds makes it suitable for creating vibrant and long-lasting colors in fabrics and other materials.
Used in Anti-bacterial and Anti-fungal Applications:
5-CHLORO-2-HYDROXY-BENZOIC ACID HYDRAZIDE is used as an anti-bacterial and anti-fungal agent for inhibiting the growth of microorganisms. Its broad-spectrum activity makes it a potential candidate for use in various applications, such as disinfectants, sanitizers, and preservatives, to maintain cleanliness and prevent the spread of infections.

InChI:InChI=1/C7H7ClN2O2/c8-4-1-2-6(11)5(3-4)7(12)10-9/h1-3,11H,9H2,(H,10,12)

Upstream product

• 15196-83-5 5-chlorosalicylic acid ethyl ester 
• 4068-78-4 methyl 5-chloro-2-hydroxybenzoate 
• 302-01-2 hydrazine 

Downstream Products

• 2491-98-7 C₁₄H₈Cl₂N₂O₃ 

Relevant articles and documents

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.

Synthesis, α-glucosidase inhibition, and molecular docking studies of novel N-substituted hydrazide derivatives of atranorin as antidiabetic agents

A series of novel N-substituted hydrazide derivatives were synthesized by reacting atranorin, a compound with a natural depside structure (1), with a range of hydrazines. The natural product and 12 new analogues (2–13) were investigated for inhibition of α-glucosidase. The N-substituted hydrazide derivatives showed more potent inhibition than the original. The experimental results were confirmed by docking analysis. This study suggests that these compounds are promising molecules for diabetes therapy. Molecular dynamics simulations were carried out with compound 2 demonstrating the best docking model using Gromac during simulation up to 20 ns to explore the stability of the complex ligand-protein. Furthermore, the activity of all synthetic compounds 2–13 against a normal cell line HEK293, used for assessing their cytotoxicity, was evaluated.

Synthesis, biological evaluation, and molecular docking studies of pyrazolyl-acylhydrazone derivatives as novel anticancer agents

A series of pyrazolyl-acylhydrazone derivatives (1e-20e) have been designed and synthesized and their biologic activities were also evaluated for telomerase inhibition and tumor cell antiproliferation. Among all the compounds, 12e showed the most potent activity in vitro, which inhibited the growth of MCF-7 and B16-F10 cell lines with IC50 values of 0.57 ± 0.03 and 0.49 ± 0.07 μM, respectively. Compound 12e also exhibited significant telomerase inhibitory activity (IC50 = 1.9 ± 0.43 μM). The result of flow cytometry demonstrated that compound 12e induced cell apoptosis. Docking simulation was performed to insert compound 12e into the crystal structure of telomerase at ATP binding site to determine the probable binding model. Based on the preliminary results, compound 12e with potent inhibitory activity in tumor growth may be a potential anticancer agent.