4959-60-8

Basic information

• Product Name: 3,4-DIMETHOXY-6-NITROBENZAMIDE
• Synonyms: 3,4-DIMETHOXY-6-NITROBENZAMIDE;4,5-DIMETHOXY-2-NITROBENZAMIDE;4,5-Dimethoxynitrobenzamide;5-DiMethoxy-2-nitrobenzaMide;2-Carbamoyl-4,5-dimethoxynitrobenzene;4,5-Dimethoxy-2-nitrobenzamide97%;Benzamide, 4,5-dimethoxy-2-nitro-
• CAS NO: 4959-60-8
• Molecular Formula: C₉H₁₀N₂O₅
• Molecular Weight: 226.19
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 4959-60-8.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 336.8 °C at 760 mmHg
• Flash Point: 157.5 °C
• Appearance: /
• Density: 1.346 g/cm³
• Vapor Pressure: 0.000109mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Acetonitrile (Slightly), DMSO (Slightly), Water (Slightly, Heated)
• CAS DataBase Reference: 3,4-DIMETHOXY-6-NITROBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHOXY-6-NITROBENZAMIDE(4959-60-8)
• EPA Substance Registry System: 3,4-DIMETHOXY-6-NITROBENZAMIDE(4959-60-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 4959-60-8(Hazardous Substances Data)

Usage

General Description

3,4-DIMETHOXY-6-NITROBENZAMIDE is a chemical compound with the molecular formula C10H10N2O5. It is a yellow solid that is commonly used in organic synthesis and as a reagent in chemical reactions. 3,4-DIMETHOXY-6-NITROBENZAMIDE is a derivative of benzamide and contains both methoxy and nitro functional groups on the benzene ring. 3,4-DIMETHOXY-6-NITROBENZAMIDE has a variety of applications, including as a building block in the synthesis of pharmaceuticals and agrochemicals, as well as in the production of dyes and pigments. It is important to handle this chemical with care, as it may pose hazards to human health and the environment if not properly managed.

InChI:InChI=1/C9H10N2O5/c1-15-7-3-5(9(10)12)6(11(13)14)4-8(7)16-2/h3-4H,1-2H3,(H2,10,12)

Upstream product

• 1336-21-6 ammonium hydroxide 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 29568-78-3 4,5-dimethoxy-2-nitrobenzoyl chloride 

Downstream Products

• 911418-25-2 tert-butyl 5-(2-[(3-phenyl)phenyl]-7-methoxy-6-(2-(4-methylpiperazin-1-yl)ethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate 
• 911418-16-1 tert-butyl 5-(6-(2-tert-butoxy-2-oxoethoxy)-2-[(3-phenyl)phenyl]-7-methoxyquinazolin-4-ylamino)-1H-indazole-1-carboxylate 
• 911418-05-8 tert-butyl 5-(6-(2-chloroethoxy)-2-(3-fluoro-4-(phenyl)phenyl)-7-methoxyquinazolin-4-ylamino)-1H-indazole-1-carboxylate 
• 911418-03-6 tert-butyl 5-(6-acetoxy-2-(3-fluoro-4-(phenyl)phenyl)-7-methoxyquinazolin-4-ylamino)-1H-indazole-1-carboxylate 
• 911418-21-8 tert-butyl 5-(6-(2-chloroethoxy)-2-[(3-phenyl)phenyl]-7-methoxyquinazolin-4-ylamino)-1H-indazole-1-carboxylate 
• 911418-19-4 tert-butyl 5-(2-[3-(phenyl)phenyl]-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate 
• 911418-14-9 tert-butyl 5-(6-acetoxy-2-[(3-phenyl)phenyl]-7-methoxyquinazolin-4-ylamino)-1H-indazole-1-carboxylate 
• 911418-04-7 tert-butyl 5-(2-(3-fluoro-4-(phenyl)phenyl)-6-hydroxy-7-methoxyquinazolin-4-ylamino)-1H-indazole-1-carboxylate 
• 911418-15-0 tert-butyl 5-(2-[(3-phenyl)phenyl]-6-hydroxy-7-methoxyquinazolin-4-ylamino)-1H-indazole-1-carboxylate 
• 911418-17-2 2-(4-(1H-indazol-5-ylamino)-2-[(3-phenyl)phenyl]-7-methoxyquinazolin-6-yloxy)acetic acid 
• 911418-01-4 2-(3-fluoro-4-(phenyl)phenyl)-7-methoxy-4-oxo-3,4-dihydroquinazolin-6-yl acetate 
• 911418-02-5 4-chloro-2-(3-fluoro-4-(phenyl)phenyl)-7-methoxyquinazolin-6-yl acetate 
• 911417-97-5 C₂₂H₁₉FN₂O₄ 
• 911417-99-7 2-(3-fluoro-4-(phenyl)phenyl)-6,7-dimethoxyquinazolin-4(3H)-one 

Relevant articles and documents

Anthranilamide-based 2-phenylcyclopropane-1-carboxamides, 1,1'-biphenyl-4-carboxamides and 1,1'-biphenyl-2-carboxamides: Synthesis biological evaluation and mechanism of action

Several anthranilamide-based 2-phenylcyclopropane-1-carboxamides 13a-f, 1,1’-biphenyl-4-carboxamides 14a-f and 1,1’-biphenyl-2-carboxamides 17a-f were obtained by a multistep procedure starting from the (1S,2S)-2-phenylcyclopropane-1-carbonyl chloride 11, the 1,1'-biphenyl-4-carbonyl chloride 12 or the 1,1'-biphenyl-2-carbonyl chloride 16 with the appropriate anthranilamide derivative 10a-f. Derivatives 13a-f, 14a-f and 17a-f showed antiproliferative activity against human leukemia K562?cells. Among these derivatives 13b, 14b and 17b exerted a particular cytotoxic effect on tumor cells. Derivative 17b showed a better antitumoral effect on K562?cells than 13b and 14b. Analyses performed to explore 17b mode of action revealed that it induced an arrest in G2/M phase of cell cycle which was consequent to DNA lesions as demonstrated by the increase in phospho-ATM and γH2AX, two known markers of DNA repair response system. The effect of 17b was also related to ROS generation, activation of JNK and induction of caspase-3 dependent apoptosis.

Synthesis, antiproliferative activity and possible mechanism of action of novel 2-acetamidobenzamides bearing the 2-phenoxy functionality

Several new 2-(2-phenoxyacetamido)benzamides 17a-v, 21 and 22 were synthesized by stirring in pyridine the acid chlorides 16a-e and the appropriate5-R-4-R1-2-aminobenzamide 15a-e and initially evaluated in vitro for antiproliferative activity against the K562 (human chronic myelogenous leukemia) cell line. Some of synthesized compounds were evaluated for their in vitro antiproliferative activity against the full NCI tumor cell line panel derived from nine clinically isolated cancer types (leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate and breast). The most active compounds caused an arrest of K562 cells in the G0-G1 phase of cell cycle and induction of apoptosis, which was mediated by caspase activation.

Design and synthesis of 6,7-dimethoxyquinazoline analogs as multi-targeted ligands for α1- and AII-receptors antagonism

Multiple-targeted ligands can have certain advantages for the management of hypertension which has multiple controls. Molecules with dual bioactivities are available in literature for treating metabolic disorders like diabetes, hypertension and hypercholesterolemia. After scrutinizing the SAR of prazosin-type α1-blockers and AII-antagonists it was planned to develop dual α1- and AII-antagonists. Five series of quinazoline derivatives were synthesized and evaluated as dual α1- and AII-antagonists on rat aortic strips for the blockade of known α1- and AII-agonist mediated contractions. Many compounds showed balanced activity on both the receptors but compound (22) was found to be the most active derivative having higher antagonistic activity on both the receptors. In the in vivo experiments the chosen compound (22) was slightly less active than prazosin but was found to be equipotent to losartan. These findings shed a new light on the structural requirements for both α1- as well as AII-receptor antagonists.