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Usage

Uses

Used in Pharmaceutical Research:
5-NITRO-2-(1-PYRROLIDINYL)BENZENECARBOXYLIC ACID is used as a building block for the synthesis of various drug candidates, leveraging its molecular structure to create new therapeutic agents.
Used in Anti-Inflammatory Drug Development:
In the pharmaceutical industry, 5-NITRO-2-(1-PYRROLIDINYL)BENZENECARBOXYLIC ACID is utilized as a key component in the development of anti-inflammatory drugs, capitalizing on its ability to modulate inflammatory responses.
Used in Anti-Cancer Drug Development:
Similarly, 5-NITRO-2-(1-PYRROLIDINYL)BENZENECARBOXYLIC ACID is employed in the creation of anti-cancer drugs, where its potential to modulate immune responses is harnessed to combat cancer cells.
It is crucial to handle 5-NITRO-2-(1-PYRROLIDINYL)BENZENECARBOXYLIC ACID with caution due to its potential toxicity and adverse effects, ensuring safety in research and development processes.

InChI:InChI=1/C11H12N2O4/c14-11(15)9-7-8(13(16)17)3-4-10(9)12-5-1-2-6-12/h3-4,7H,1-2,5-6H2,(H,14,15)/p-1

Upstream product

• 123-75-1 pyrrolidine 
• 2516-96-3 2-chloro-5-nitrobenzoic acid 
• 445-29-4 o-fluoro-benzoic acid 
• 7304-32-7 2-fluoro-5-nitrobenzoic acid 

Downstream Products

• 10220-22-1 1-(4-nitro-phenyl)-pyrrolidine 
• 19555-57-8 7-Nitro-perhydropyrrolo<1,2-b>benz-1,3-oxazin-5-on 
• 16089-46-6 5-amino-2-pyrrolidino-benzoic acid 
• 78252-34-3 methyl 4-(2-(5-chloro-2-pyrrolidino-benzoylamino)-ethyl)-benzoate 
• 77265-94-2 5-chloro-2-(1-pyrrolidinyl)benzoic acid 

Relevant academic research and scientific papers

Discovery of novel N-benzylbenzamide derivatives as tubulin polymerization inhibitors with potent antitumor activities

A series of novel N-benzylbenzamide derivatives were designed and synthesized as tubulin polymerization inhibitors. Among fifty-one target compounds, compound 20b exhibited significant antiproliferative activities with IC50 values ranging from 12 to 27 nM against several cancer cell lines, and possessed good plasma stability and satisfactory physicochemical properties. Mechanism studies demonstrated that 20b bound to the colchicine binding site and displayed potent anti-vascular activity. Notably, the corresponding disodium phosphate 20b-P exhibited an excellent safety profile with the LD50 value of 599.7 mg/kg (i.v. injection), meanwhile, it significantly inhibited tumor growth and decreased microvessel density in liver cancer cell H22 allograft mouse model without obvious toxicity. Collectively, 20b and 20b-P are novel promising anti-tubulin agents with more druggable properties and deserve to be further investigated for cancer therapy.

Catalyst-free microwave-assisted amination of 2-chloro-5-nitrobenzoic acid

(Chemical Equation Presented) The synthesis of N-substituted 5-nitroanthranilic acid derivatives 3a-w was achieved by a new, mild, microwave-assisted, regioselective amination reaction of 5-nitro-2-chlorobenzoic acid (1a) with a diverse range of aliphatic

Ultrasound-promoted reaction of 2-chlorobenzoic acids and aliphatic amines

An improvement to the use of DMF as a solvent for the condensation of 2-chlorobenzoic acids with aliphatic primary or secondary amines was described. A number of alkylaminobenzoic acids and dialkylaminobenzoic acids were synthesized in acceptable-to-good yield. The advantages of this procedure include readily available substrates, the use of an inexpensive copper powder without taking any precautions to exclude moisture under mild conditions and experimental ease. Furthermore, this condensation could also be achieved under nonclassical conditions by using ultrasonic irradiation at room temperature. We demonstrated that ultrasound-promoted condensation of 2-chlorobenzoic acid with aliphatic amines with the use of DMF as the solvent, especially in the case of secondary amines, affords products in high yields and reduces the reaction time to minutes. The results proved to be highly reproducible because the relevant sonochemical parameters were rigorously controlled. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Repaglinide and related hypoglycemic benzoic acid derivatives

The structure-activity relationships in two series of hypoglycemic benzoic acid derivatives (5, 6) were investigated. Series 5 resulted from meglitinide (3) when the 2-methoxy was replaced by an alkyleneimino residue. Maximum activity was observed with the cis-3,5-dimethylpiperidino (5h) and the octamethyleneimino (5l) residues. Series 6 resulted from the meglitinide analogon 4 bearing an inversed amido function when the 2-methoxy, the 5- fluoro, and the α-methyl residue were replaced by a 2-piperidino, a 5- hydrogen, and a larger α-alkyl residue, respectively. An alkoxy residue ortho to the carboxy group further increased activity and duration of action in the rat. The most active racemic compound, 6al (R4 = isobutyl; R = ethoxy), turned out to be 12 times more active than the sulfonylurea (SU) glibenclamide (1). Activity was found to reside predominantly in the (S)- enantiomers. Compared with the SUs 1 and 2 (glimepiride), the most active enantiomer, (S)-6al (AG-EE 623 ZW; repaglinide; ED50 = 10 μg/kg po), is 25 and 18 times more active. Repaglinide turned out to be a useful therapeutic for type 2 diabetic patients; approval was granted recently by the FDA and the EMEA. From investigations on the pharmacophoric groups in compounds of type 5 and 6, it was concluded that in addition to the two already known - the acidic group (COOH; S02NH) and the amidic spacer (CONH; NHCO) - the ortho residue R1 (alkyleneimino; alkoxy; oxo) must be regarded as a third one. A general pharmacophore model suitable for hypoglycemic benzoic acid derivatives, SUs, and sulfonamides is proposed (Figure 6). Furthermore, from superpositions of low-energy conformations (LECs) of 1, 2, and (S)-6al, it was concluded that a common binding conformation (LEC II; Figure 10B) may exist and that differences in binding to the SU receptor and in the mechanism of insulin release between repaglinide and the two SUs may be due to specific hydrophobic differences.