52313-55-0

Basic information

• Product Name: N-(1-benzyl-4-piperidyl)benzohydrazide
• CAS NO: 52313-55-0
• Molecular Formula: C₁₉H₂₃N₃O
• Molecular Weight: 309.411
• Mol File: 52313-55-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 426°Cat760mmHg
• Flash Point: 211.4°C
• Density: 1.16g/cm³
• CAS DataBase Reference: N-(1-benzyl-4-piperidyl)benzohydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1-benzyl-4-piperidyl)benzohydrazide(52313-55-0)
• EPA Substance Registry System: N-(1-benzyl-4-piperidyl)benzohydrazide(52313-55-0)

Safety Data

• Hazardous Substances Data: 52313-55-0(Hazardous Substances Data)

Upstream product

• 3612-20-2 1-phenylmethyl-4-piperidone 
• 613-94-5 benzoic acid hydrazide 
• 52313-53-8 N'-(1-benzylpiperidin-4-ylidene)benzohydrazide 

Downstream Products

• 1185303-13-2 (1-benzyl-piperidin-4-yl)-hydrazine dihydrochloride 
• 65-85-0 benzoic acid 

Relevant articles and documents

Discovery of potent and selective inhibitors of the mammalian target of rapamycin (mTOR) kinase

The mammalian target of rapamycin (mTOR) is a central regulator of cell growth, metabolism, and angiogenesis and an emerging target in cancer research. High throughput screening (HTS) of our compound collection led to the identification of 3-(4-morpholin-4-yl-1-piperidin-4-yl-1H-pyrazolo[3,4-d] pyrimidin-6-yl)phenol (5a), a modestly potent and nonselective inhibitor of mTOR and phosphoinositide 3-kinase (PI3K). Optimization of compound 5a, employing an mTOR homology model based on an X-ray crystal structure of closely related PI3Kγ led to the discovery of 6-(1H-indol-5-yl)-4-morpholin-4-yl-1-[1- (pyridin-3-ylmethyl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine (5u), a potent and selective mTOR inhibitor (mTOR IC50 = 9 nM; PI3Kα IC 50 = 1962 nM). Compound 5u selectively inhibited cellular biomarker of mTORC1 (P-S6K, P-4EBP1) and mTORC2 (P-AKT S473) over the biomarker of PI3K/PDK1 (P-AKT T308) and did not inhibit PI3K-related kinases (PIKKs) in cellular assays. These pyrazolopyrimidines represent an exciting new series of mTOR-selective inhibitors with potential for development for cancer therapy. 2009 American Chemical Society.

Discovery of 4-morpholino-6-aryl-1H-pyrazolo[3,4-d]pyrimidines as highly potent and selective ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR): Optimization of the 6-aryl substituent

Design and synthesis of a series of 4-morpholino-6-aryl-1H-pyrazolo[3,4-d] pyrimidines as potent and selective inhibitors of the mammalian target of rapamycin (mTOR) are described. Optimization of the 6-aryl substituent led to the discovery of inhibitors carrying 6-ureidophenyl groups, the first reported active site inhibitors of mTOR with subnanomolar inhibitory concentrations. The data presented in this paper show that 6-arylureidophenyl substituents led to potent mixed inhibitors of mTOR and phosphatidylinositol 3-kinase α (PI3K-α), whereas 6-alkylureidophenyl appendages gave highly selective mTOR inhibitors. Combination of 6-alkylureidophenyl groups with 1-carbamoylpiperidine substitution resulted in compounds with subnanomolar IC50 against mTOR and greater than 1000-fold selectivity over PI3K-α. In addition, structure based drug design resulted in the preparation of several 6-arylureidophenyl-1H-pyrazolo[3,4-d]pyrimidines, substituted in the 4-position of the arylureido moiety with water solubilizing groups. These compounds combined potent mTOR inhibition (IC50501 nM). 2009 American Chemical Society.