4959-60-8

Usage

Uses

Used in Pharmaceutical Synthesis:
3,4-DIMETHOXY-6-NITROBENZAMIDE is used as a building block in the synthesis of pharmaceuticals for its versatile chemical properties. Its presence in the molecular structure can influence the activity and selectivity of the resulting compounds, making it a valuable component in drug development.
Used in Agrochemical Production:
In the agrochemical industry, 3,4-DIMETHOXY-6-NITROBENZAMIDE is utilized as a key intermediate in the production of various agrochemicals. Its chemical structure allows for the creation of compounds that can be effective in controlling pests and diseases in agriculture.
Used in Dyes and Pigments Manufacturing:
3,4-DIMETHOXY-6-NITROBENZAMIDE is also used in the manufacturing of dyes and pigments due to its color-producing properties. Its chemical composition contributes to the color intensity and stability of the final products, which are used in a wide range of applications, including textiles, plastics, and printing inks.
It is important to handle 3,4-DIMETHOXY-6-NITROBENZAMIDE with care, as it may pose hazards to human health and the environment if not properly managed. Proper safety measures and disposal methods should be followed to minimize any potential risks associated with its use.

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

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

Downstream Products

• 5004-88-6 4,5-dimethoxyanthranilamide 
• 202475-60-3 WHI-P₁₃₁ 
• 211555-04-3 4-(3-bromo-4-hydroxyphenyl)amino-6,7-dimethoxyquinazoline 
• 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 

Relevant academic research and scientific papers

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.

Copper-Catalyzed One-pot Synthesis of Pyrimidines from Amides, N,N′-dimethylformamide dimethylacetal, and Enamines

A versatile copper catalyzed one-pot synthesis of diversely substituted pyrimidines directly from amides, N,N′-dimethylformamide dimethylacetal (DMF?DMA) and enamines has been established. The reaction involved the two C?N bonds and one C?C bond formation by formal [2+1+3] annulation approach to pyrimidines. This protocol is based on the use of readily available primary amides, DMF?DMA and enamines to install di- and tri-substituted pyrimidine structure with diverse functionality in one-pot manner, which makes this strategy to be appealing for the medicinal chemistry. (Figure presented.).

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.

2-Cinnamamido, 2-(3-phenylpropiolamido), and 2-(3-phenylpropanamido) benzamides: Synthesis, antiproliferativeactivity, and mechanism of action

Several new benzamides 4a-q were synthesized by stirring in pyridine the acid chlorides 3a-q with the appropriate anthranilamide derivatives 2a-g. Some of the synthesized compounds were evaluated for their in vitro antiproliferative activity against a panel of 5 human cell lines (K562 human chronic myelogenous leukemia cells, MCF-7 breast cancer cells, HTC-116 and HT26 colon cancer cells and NCI H460 non-small cell lung cancer cells).

RHO KINASE INHIBITORS

The present invention relates to inhibitors of ROCK1 and ROCK2, which may be selective for ROCK2, and methods of modulating the pharmacokinetic and/or pharmacodynamic properties of such compounds. Also provided are methods of inhibiting ROCK1 and/or ROCK2. Also provided are treatments combining inhibitors of ROCK1 and/or ROCK2 with statins.

QUINAZOLINE DERIVATIVE USEFUL AS TOLL-LIKE RECEPTOR ANTAGONIST

Compound CPG 52364 having formula (I) and pharmaceutically acceptable salts thereof are inhibitors of signaling by Toll-like receptors TLR7, TLR8, and TLR9, and they are useful in treatment of unwanted Immune activity. Pharmaceutical composition including

RHO KINASE INHIBITORS

The present invention relates to inhibitors of ROCKl and R0CK2, which may be selective for R0CK2, and methods of modulating the pharmacokinetic and/or pharmacodynamic properties of such compounds. Also provided are methods of inhibiting ROCKl and/or R0CK2. Also provided are treatments combining inhibitors of ROCKl and/or R0CK2 with statins.

PHARMACOKINETICALLY IMPROVED COMPOUNDS

The present invention relates to inhibitors of ROCKl and R0CK2 and methods of modulating the pharmacokinetic and/or pharmacodynamic properties of such compounds. Also provided are methods of inhibiting ROCKl and or R0CK2 that are useful for the treatment of disease.

Phenylarsonic acid compounds with broad-spectrum and potent cytotoxic activity against human cancer cells

The in vitro cytotoxic activity profile of nine novel phenylarsonic acid (CAS 98-05-5, PAA) compounds against 17 human cancer cell lines including (a) ovarian cancer cell lines ES-2, PA-1, CAOV-3, OVCAR-3, (b) testicular cancer cell lines Ntera-2, Tera-2, N2NICP, 833K, and 64CP, (c) multiple myeloma cell lines ARH77, HS-Sultan, RPMI-8226, and U266, and (d) acute lymphoblastic leukemia (ALL) cell lines NALM-6, MOLT-3, ALL-1, and RS4; 11, was determined by the MTT assay. The lead compounds, 2-methylthio4- [(4′-aminophenylazo)-phenylarsonic acid] pyrimidine (PHI-370) and 2-methylthio-4-(4′-phenylarsonic acid)-aminopyrimidine (PHI-380) caused apoptotic death in all 17 cancer cell lines at low micromolar concentrations, as documented by TUNEL assays and confocal laser scanning microscopy. PHI-380 was also tested and found to be very active against primary tumor cells isolated from surgical biopsy specimens of 14 patients with therapy-refractory non-small cell lung cancer, breast cancer, colon cancer, lymphoma, hepatoblastoma, or Wilm's tumor as well. Because of their broad-spectrum and potent anticancer activity and ability to induce apoptosis in primary tumor cells from therapy-refractory cancer patients, PAA compounds such as PHI-370 and PHI-380 may provide the basis for effective salvage regimens for patients with recurrent cancer.