241499-44-5

Basic information

• Product Name: TERT-BUTYL 4-(4-ISOPROPYLANILINO)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE
• Synonyms: TERT-BUTYL 4-(4-ISOPROPYLANILINO)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE;1-BOC-4-[(4-ISOPROPYLPHENYL)AMINO]-PIPERIDINE
• CAS NO: 241499-44-5
• Molecular Formula: C₁₉H₃₀N₂O₂
• Molecular Weight: 318.45
• Mol File: 241499-44-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 99-100°
• Appearance: /
• CAS DataBase Reference: TERT-BUTYL 4-(4-ISOPROPYLANILINO)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 4-(4-ISOPROPYLANILINO)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE(241499-44-5)
• EPA Substance Registry System: TERT-BUTYL 4-(4-ISOPROPYLANILINO)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE(241499-44-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 241499-44-5(Hazardous Substances Data)

Upstream product

• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 99-88-7 4-Isopropylaniline 

Downstream Products

• 680191-41-7 4-[N-(3,4-dimethylbenzyl)-N-(4-isopropylphenyl)amino]piperidine 
• 241499-46-7 4-[N-(4-isopropylphenyl)-N-(3-methyl-2-butenyl)amino]piperidine 
• 680191-38-2 N-(tert-butoxycarbonyl)-4-[N-(3,4-dimethylbenzyl)-N-(4-isopropylphenyl)amino]piperidine 
• 241499-45-6 N-(tert-butoxycarbonyl)-4-[N-(4-isopropylphenyl)-N-(3-methyl-2-butenyl)amino]piperidine 

Relevant articles and documents

N-[4-(Methylsulfonylamino)benzyl]thiourea analogues as vanilloid receptor antagonists: Analysis of structure-activity relationships for the 'C-Region'

We recently reported that N-(4-t-butylbenzyl)-N′-[4- (methylsulfonylamino)benzyl] thiourea (2) was a high affinity antagonist of the vanilloid receptor with a binding affinity of Ki=63 nM and an antagonism of Ki=53.9 nM in rat VR1 heterologously expressed in Chinese hamster ovary (CHO) cells (Mol. Pharmacol. 2002, 62, 947-956). In an effort to further improve binding affinity and antagonistic potency, we have modified the C-region of the lead 4-t-butylbenzyl group with diverse surrogates, such as araalkyl, alkyl, 4-alkynylbenzyl, indanyl, 3,3-diarylpropyl, 4-alkoxybenzyl, 4-substituted piperazine and piperidine. The lipophilic surrogates, arylalkyl and alkyl, conferred modest decreases in binding affinities and antagonistic potencies; the groups having heteroatoms resulted in dramatic decreases. Our findings indicate that 4-t-butylbenzyl is one of the most favorable groups for high receptor binding and potent antagonism to VR1 in this structural series.

The discovery of [1-(4-Dimethylamino-benzyl)-piperidin-4-yl]-[4-(3,3-dimethylbutyl)-phenyl]-(3-methyl-but-2-enyl)-amine, an N-type Ca+2 channel blocker with oral activity for analgesia

Our drug discovery efforts for N-type calcium channel blockers in the 4-piperidinylaniline series led to the discovery of an orally active analgesic agent 26. 1-[4-Dimethylamino-benzyl)-piperidin-4-yl]-[4-(3,3-dimethyl-butyl)-phenyl]-(3-methyl-but-2-enyl)-amine (26) showed high affinity to functionally block N-type calcium channels (IC50=0.7 μM in the IMR32 assay) and exhibited high efficacy in the anti-writhing analgesia test with mice (ED50=12 mg/kg by po and 4 mg/kg by iv). In this report, the rationale for the design, synthesis, biological evaluation, and pharmacokinetics of this series of blockers is described. Copyright (C) 2000 Elsevier Science Ltd.