1443-76-1

Basic information

• Product Name: 3,5-DIMETHOXY-4-HYDROXYBENZHYDRAZIDE
• Synonyms: 4-HYDROXY-3,5-DIMETHOXYBENZHYDRAZIDE;4-HYDROXY-3,5-DIMETHOXYBENZOHYDRAZIDE;3,5-DIMETHOXY-4-HYDROXYBENZHYDRAZIDE;SYRINGIC ACID HYDRAZIDE;SYRINGHYDRAZIDE
• CAS NO: 1443-76-1
• Molecular Formula: C₉H₁₂N₂O₄
• Molecular Weight: 212.2
• EINECS: 215-884-5
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes
• Mol File: 1443-76-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 156-157°C
• Boiling Point: 379.5°Cat760mmHg
• Flash Point: 155°C
• Appearance: /
• Density: 1.335g/cm³
• Refractive Index: 1.575
• PKA: 8.63±0.25(Predicted)
• BRN: 2657142
• CAS DataBase Reference: 3,5-DIMETHOXY-4-HYDROXYBENZHYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIMETHOXY-4-HYDROXYBENZHYDRAZIDE(1443-76-1)
• EPA Substance Registry System: 3,5-DIMETHOXY-4-HYDROXYBENZHYDRAZIDE(1443-76-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 1443-76-1(Hazardous Substances Data)

Usage

Description

3,5-DIMETHOXY-4-HYDROXYBENZHYDRAZIDE is a chemical compound with the molecular formula C10H14N2O4, belonging to the class of hydrazine and benzene derivatives. It features hydroxy and methoxy functional groups, which contribute to its potential pharmacological properties, such as antioxidant and anti-inflammatory effects. 3,5-DIMETHOXY-4-HYDROXYBENZHYDRAZIDE has been explored for its therapeutic potential in various medical applications, including neurodegenerative diseases and cancer therapy, as well as in the synthesis of other organic molecules and as a reagent in chemical reactions.

Uses

Used in Pharmaceutical Industry:
3,5-DIMETHOXY-4-HYDROXYBENZHYDRAZIDE is used as a drug candidate for its potential antioxidant and anti-inflammatory properties, which may contribute to the treatment of various diseases and conditions.
Used in Neurodegenerative Disease Treatment:
In the field of neurology, 3,5-DIMETHOXY-4-HYDROXYBENZHYDRAZIDE is used as a potential therapeutic agent for neurodegenerative diseases, leveraging its pharmacological properties to mitigate disease progression and symptoms.
Used in Cancer Therapy:
3,5-DIMETHOXY-4-HYDROXYBENZHYDRAZIDE is utilized as a drug candidate in oncology, where it is being investigated for its potential to target and treat cancer cells, offering a novel approach to cancer treatment.
Used in Organic Synthesis:
In the chemical industry, 3,5-DIMETHOXY-4-HYDROXYBENZHYDRAZIDE serves as a key intermediate in the synthesis of other organic molecules, contributing to the development of new compounds with various applications.
Used as a Chemical Reaction Reagent:
3,5-DIMETHOXY-4-HYDROXYBENZHYDRAZIDE is employed as a reagent in chemical reactions, facilitating specific transformations and processes in the synthesis of target molecules.

InChI:InChI=1/C9H12N2O4/c1-14-6-3-5(9(13)11-10)4-7(15-2)8(6)12/h3-4,12H,10H2,1-2H3,(H,11,13)

Upstream product

• 50597-60-9 3,5-dimethoxy-4-hydroxybenzoic acid chloride 
• 884-35-5 methyl syringate 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 3943-80-4 4-hydroxy-3,5-dimethoxybenzoic acid ethyl ester 

Relevant articles and documents

Synthesis, biological evaluation and docking studies of 1,3,4-oxadiazole fused benzothiazole derivatives for anticancer drugs

Background: Hetero atom containing compounds are well studied class of organic compounds exhibits variety of properties and applications. Design and synthesis of new heterocyclic compounds are always of great interest in synthetic and medicinal organic chemistry. Benzothiazole or 2-aminobenzothiazole scaffold based derivatives were reported to display a wide range of biological activities including anticancer, anti-tubercular, antiviral, fungicidal, etc. On the other hand, 1,3,4-oxadiazoles were permit to increase their biological activities due to H-bonding with receptors. These derivatives possess diverse biological activities which include anticancer, antiviral, antifungal, antibacterial and antidepressant etc. Due to interesting biological activity information of about these hetero cyclic moieties, benzothiazole/2-aminobenzothiazole and 1,3,4-oxadiazoles moieties, we chose to design a new series of heterocyclic compounds by mimicking these two types of scaffolds in a single molecule for our study. Methods: The 1,3,4-oxadiazole linked benzothiazole derivatives were synthesized by condensation of, 2-(4-(5-(benzo[d]thiazol-2-yl)-1,3,4-thiadiazol-2-yl)-2,6-dimethoxyphenoxy)acetohydrazide and POCl3 under reflux conditions. All these ten compounds structures were confirmed by spectral data1H &13C NMR, Mass, CHN analysis etc. Further, these compounds were evaluated for their anticancer activity against four human cancer cell lines, A549, MCF7, A375 and HT-29 in comparison to CA4 as a reference drug. We also carried out docking studies of these compounds in the Colchicines binding site of Tubulin (PDB_ID: 1SA0) using Glide docking tool indicated that the ligands show good interactions with active site residues. Results: A new series of 1,3,4-oxadiazole fused benzothiazole derivatives were synthesized successfully in totally six steps starting with 4-hydroxy-3,5-dimethoxybenzoyl chloride. All these newly synthesized compounds structures were confirmed by spectral studies and elemental analysis. As we designed for anticancer activity, they were assessed for their anticancer activity against four human cancer cell lines in comparison to a reference drug CA4. As expected, all the ten compounds exhibited anticancer activities against four cancer cell lines with half maximal inhibitory concentration (IC50) values ranging from 0.01 μM to 12.3 μM. The docking studies indicated all the compounds exhibited good binding energies with the receptor. Conclusion: In this study we designed a new series heterocyclic compounds by mimicking two types of scaffolds benzothiazole/2-aminobenzothiazole and 1,3,4-oxadiazoles moieties in a single molecule based on their biological activity in the literature. They were synthesized successfully and molecular structures were confirmed by spectral studies. As expected, all the compounds exhibited anticancer activities against four cancer cell lines. This study can provide a roadmap for design and synthesis of new drug molecules for antitumor and anticancer activity.