92033-81-3

Usage

Chemical class

Pyrrolidines A type of organic compound that contains a pyrrolidine ring, which is a five-membered ring with one nitrogen atom and four carbon atoms.

Structural features

Nitrogen atom with a propyl chain The nitrogen atom in the pyrrolidine ring is connected to a propyl chain (three carbon atoms), which is a common structural feature in many organic compounds.

4-nitrophenoxy group

A functional group attached to the propyl chain This group consists of a phenol (hydroxyl group attached to a benzene ring) with a nitro group (-NO2) attached to the para position (4th position) of the benzene ring.

Potential applications

Pharmaceuticals and agrochemicals Due to its structural features, 1-(3-(4-nitrophenoxy)propyl)pyrrolidine may have potential uses in the development of drugs and agrochemicals, as it can mimic biological molecules and form interactions with biological targets.

Ability to mimic biological molecules

Structural similarity to natural compounds The presence of the pyrrolidine ring and the 4-nitrophenoxy group allows 1-(3-(4-nitrophenoxy)propyl)pyrrolidine to potentially mimic the structure and function of natural biological molecules, making it a candidate for drug development.

Interactions with biological targets

Potential for binding and modulation The compound's structural features may enable it to form interactions with specific biological targets, such as enzymes, receptors, or other proteins, which could be useful in the development of new drugs or agrochemicals.

Synthesis

A valuable compound for further research The synthesis of 1-(3-(4-nitrophenoxy)propyl)pyrrolidine and its properties make it an interesting compound for researchers to study and potentially develop for various applications.

Potential development

Various fields The compound's unique structure and properties may lead to its development in a range of fields, including pharmaceuticals, agrochemicals, and other areas of chemical research.

Upstream product

• 123-75-1 pyrrolidine 
• 13094-50-3 1-(3-bromopropoxy)-4-nitrobenzene 
• 19748-66-4 3-pyrrolidin-1-yl-propan-1-ol 
• 350-46-9 4-Fluoronitrobenzene 

Downstream Products

• 343965-79-7 1-{3-[(4-aminophenyl)oxy]propyl}pyrrolidine 
• 1394355-84-0 C₁₆H₂₀N₂O₂S₂ 
• 1394355-93-1 C₃₀H₂₉N₃O₄S₂ 
• 1394355-94-2 C₃₀H₂₉N₃O₄S₂ 
• 1394355-95-3 C₃₀H₂₉N₃O₄S₂ 

Relevant academic research and scientific papers

Discovery of 4-piperazinyl-2-aminopyrimidine derivatives as dual inhibitors of JAK2 and FLT3

Hybridization strategy is an effective strategy to obtain multi-target inhibitors in drug design. In this study, we assembled the pharmacophores of momelotinib and tandutinib to get a series of 4-piperazinyl-2-aminopyrimidine derivatives. All compounds were tested for the inhibition of JAK2 and FLT3 enzymes, of which, compounds with potent enzyme activities were assayed for antiproliferative activities against three cancer cell lines (HEL, MV4-11, and HL60). The structure-activity relationship studies were conducted through variations in two regions, the “A” phenyl ring and “B” phenyl ring. Compound 14j showed the most balanced in vitro inhibitory activity against JAK2 and FLT3 (JAK2 IC50 = 27 nM, FLT3 IC50 = 30 nM), and it also showed potent inhibition against the above tested cell lines. In the cellular context, 14j strongly induced apoptosis by arresting cell cycle in the G1/S phase, and was selected as a promising JAK2/FLT3 dual inhibitor.

Discovery of potent and selective rhodanine type IKKβ inhibitors by hit-to-lead strategy

Regulation of NF-κB activation through the inhibition of IKKβ has been identified as a promising target for the treatment of inflammatory and autoimmune disease such as rheumatoid arthritis. In order to develop novel IKKβ inhibitors, we performed high throughput screening toward around 8000 library compounds, and identified a hit compound containing rhodanine moiety. We modified the structure of hit compound to obtain potent and selective IKKβ inhibitors. Throughout hit-to-lead studies, we have discovered optimized compounds which possess blocking effect toward NF-κB activation and TNFα production in cell as well as inhibition activity against IKKβ. Among them, compound 3q showed the potent inhibitory activity against IKKβ, and excellent selectivity over other kinases such as p38α, p38β, JNK1, JNK2, and JNK3 as well as IKKα.

Synthesis, structure-activity relationships, and biological profiles of a quinazolinone class of histamine H3 receptor inverse agonists

A new series of quinazolinone derivatives was synthesized and evaluated as nonimidazole H3 receptor inverse agonists. 2-Methyl-3-(4-{[3-(1- pyrrolidinyl)propyl]oxy}phenyl)-5-(trifluoromethyl)-4(3H)-quinazolinone (1) was identified as a promising derivative for further evaluation following optimization of key parameters. Compound 1 has potent H3 inverse agonist activity and excellent selectivity over other histamine receptor subtypes and a panel of 115 unrelated diverse binding sites. Compound 1 also shows satisfactory pharmacokinetic profiles and brain penetrability in laboratory animals. Two hours after oral administration of 30 mg/kg of 1 to SD rats, significant elevation of brain histamine levels was observed where the brain H3 receptor was highly occupied (>90%). On the basis of species differences in P-glycoprotein (P-gp) susceptibility of 1 between human and rodent P-gps, the observed rodent brain permeability of 1 is significantly limited by P-gp mediated efflux in rodents, whereas the extent of P-gp mediated efflux in humans should be very small or negligible. The potential of 1 to be an efficacious drug was demonstrated by its excellent brain penetrability and receptor occupancy in P-gp-deficient CF-1 mice.

CRYSTAL OF 4(3H)-QUINAZOLINONE DERIVATIVE

A substance that has a potency antagonistic to coupling of histamine with histamine H3 receptor or a potency of inhibiting the constant activity of histamine H3 receptor. There is provided a form I crystal of 2-methy 3-{4-[3-(1-pyrrolidinyl)propoxy]phenyl}-5-trifluoromethyl-4(3H)-quinazolinone that in the powder X- ray diffractometry, has peaks at 6.4°, 9.7°, 10.2°, 12.9°, 14.2°, 14.7°, 16.0°, 16.3°, 16.8°, 17.6°, 19.5°, 20.3°, 20.6°, 21.2°, 21.8°, 22.1°, 22.4°, 22.6°, 24.0°, 24.3°, 24.9°, 25.7°, 25.9°, 26.5°, 26.7°, 27.4°, 29.1°, 29.4°, 32.3° and 39.0° diffraction angles(2θ ± 0.2°).

METHOD FOR PRODUCING 4(3H)-QUINAZOLINONE DERIVATIVE

Disclosed is a method for producing 2-methyl-3-{4- [3-(1-pyrrolidinyl)propoxy]phenyl}-5-trifluoromethyl-4(3H)-quinazolinone comprising a step for reacting 2-methyl-5-trifluoromethyl-4H-3,1-benzoxazine-4-one with 4-[3-(1-pirrolidinyl)propoxy]aniline or an acid addition salt thereof, or 4-(1-cyclobutyl-4-piperidinyl)oxyaniline or an acid addition salt thereof in the presence of an acetic acid catalyst.