78243-27-3

Usage

Derivative of piperidine and benzoic acid

2-(4-METHYLPIPERIDIN-1-YL)-5-NITROBENZOIC ACID is derived from two main structures, piperidine (a nitrogen-containing heterocyclic compound) and benzoic acid (a simple aromatic carboxylic acid), which are combined to form the given compound.

Nitro group attached to the benzene ring

The presence of a nitro group (-NO2) on the benzene ring makes 2-(4-METHYLPIPERIDIN-1-YL)-5-NITROBENZOIC ACID more reactive and versatile for various chemical reactions and transformations.

Building block in organic synthesis

2-(4-Methylpiperidin-1-yl)-5-nitrobenzoic acid is commonly used as a building block in the synthesis of more complex organic compounds, making it a valuable reagent in organic chemistry.

Pharmaceutical research

2-(4-METHYLPIPERIDIN-1-YL)-5-NITROBENZOIC ACID has potential applications in pharmaceutical research, as it can be used as an intermediate in the development of new drugs or other chemical products.

Significant role in organic chemistry and drug discovery

Due to its unique structure and reactivity, 2-(4-Methylpiperidin-1-yl)-5-nitrobenzoic acid plays an important role in the field of organic chemistry and contributes to the ongoing efforts in drug discovery and chemical research.

InChI:InChI=1/C13H16N2O4/c1-9-4-6-14(7-5-9)12-3-2-10(15(18)19)8-11(12)13(16)17/h2-3,8-9H,4-7H2,1H3,(H,16,17)/p-1

Upstream product

• 626-58-4 4-methylpiperidin 
• 2516-96-3 2-chloro-5-nitrobenzoic acid 

Downstream Products

• 113456-93-2 3-chloro-5'-nitro-2'-(4-methyl-1-piperidinyl)benzophenone 
• 132439-17-9 [5-Amino-2-(4-methyl-piperidin-1-yl)-phenyl]-(3-trifluoromethyl-phenyl)-methanone 
• 132439-15-7 [5-Amino-2-(4-methyl-piperidin-1-yl)-phenyl]-(3-chloro-phenyl)-methanone 
• 132439-16-8 [5-Amino-2-(4-methyl-piperidin-1-yl)-phenyl]-m-tolyl-methanone 
• 77266-04-7 methyl 4-(2-(5-chloro-2-(4-methyl-piperidino)-benzoylamino)-ethyl)-benzoate 
• 77266-05-8 5-chloro-2-(4-methyl-piperidino)-benzoic acid 
• 78243-68-2 5-amino-2-(4-methyl-piperidin-1-yl)-benzoic acid 
• 132439-20-4 2-(4-methyl-1-piperidinyl)-5-nitrobenzoyl chloride 

Relevant academic research and scientific papers

INHIBITORS OF THE MICROSOMAL PROSTAGLANDIN E2 SYNTHASE-1

This invention relates to compounds of formula I, their use as inhibitors of the microsomal prostaglandin E2 synthase-1 (mPGES-1), pharmaceutical compositions containing them, and their use as medicaments for the treatment and/or prevention of

New Compounds

This invention relates to compounds of formula I, their use as inhibitors of the microsomal prostaglandin E2 synthase-1 (mPGES-1), pharmaceutical compositions containing them, and their use as medicaments for the treatment and/or prevention of

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.

Synthesis and antitumor activity of novel benzophenone derivatives

Novel benzophenone derivatives were synthesized and screened for cytotoxic and antitumor activity. Friedel-Crafts condensation was employed to construct the benzophenone skeleton. Among the compounds synthesized, morpholino and thiomorpholino benzophenones 3a-d exhibited potent cytotoxic activity against P388 murine leukemia and PC-6 human lung carcinoma cells in vitro, and compounds 3a, 3c, and 3j, when administered intraperitoneally, showed significant antitumor activity against the malignant ascites caused by intraperitoneal inoculation of P388 cells in mice.

(Benzoylphenyl)piperidines: A new class of immunomodulators

A series of (benzoylphenyl)piperidines has been synthesized and evaluated for activity as immunomodulators. Several of these compounds show good activity in primary screening on the basis of the lymphocytes mitogenic response to Con A, PHA, and PWM. A chloro group in position 4 of the benzoyl moiety as well as an amino group (or a carbamate derivative) para to the piperidine nucleus seems to be essential for activity. The depicted compounds may be considered as the first examples of a new series of immunomodulators.