117654-86-1

Usage

InChI:InChI=1/C16H25NO3/c1-16(2,3)20-15(19)17(11-7-8-12-18)13-14-9-5-4-6-10-14/h4-6,9-10,18H,7-8,11-13H2,1-3H3

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 59578-63-1 4-(benzylamino)-1-butanol 
• 100-52-7 benzaldehyde 
• 99858-57-8 4-{[1-Phenyl-meth-(E)-ylidene]-amino}-butan-1-ol 
• 100-46-9 benzylamine 
• 19340-88-6 N-benzyl-4-hydroxybutanamide 

Downstream Products

• 635304-19-7 toluene-4-sulfonic acid 4-(benzyl-tert-butoxycarbonyl-amino)-butyl ester 
• 213772-01-1 4-{benzyl[(tert-butoxy)carbonyl]amino}butanoic acid 
• 400045-79-6 N-benzyl-N-(t-butoxycarbonyl)-4-amino-1-iodobutane 
• 158794-22-0 4-[N-(t-butoxycarbonyl)-N-[(phenyl)methyl]-amino]-1-methanesulfonyl butane 
• 213773-07-0 N-(N'-benzyl-N'-tert-butoxycarbonyl-4-aminobutyl)-N-tert-butoxycarbonyl-6-aminohexanoic acid 
• 213772-92-0 [4-(benzyl-tert-butoxycarbonyl-amino)-butyl]-(6-hydroxy-hexyl)-carbamic acid tert-butyl ester 
• 213772-66-8 6-[4-(N-tert-Butoxycarbonyl-N-phenylmethylamino)-butylamino]-hexan-1-ol 

Relevant academic research and scientific papers

[Co(TPP)]-Catalyzed Formation of Substituted Piperidines

Radical cyclization via cobalt(III)-carbene radical intermediates is a powerful method for the synthesis of (hetero)cyclic structures. Building on the recently reported synthesis of five-membered N-heterocyclic pyrrolidines catalyzed by CoII porphyrins, the [Co(TPP)]-catalyzed formation of useful six-membered N-heterocyclic piperidines directly from linear aldehydes is presented herein. The piperidines were obtained in overall high yields, with linear alkenes being formed as side products in small amounts. A DFT study was performed to gain a deeper mechanistic understanding of the cobalt(II)-porphyrin-catalyzed formation of pyrrolidines, piperidines, and linear alkenes. The calculations showed that the alkenes are unlikely to be formed through an expected 1,2-hydrogen-atom transfer to the carbene carbon. Instead, the calculations were consistent with a pathway involving benzyl-radical formation followed by radical-rebound ring closure to form the piperidines. Competitive 1,5-hydrogen-atom transfer from the β-position to the benzyl radical explained the formation of linear alkenes as side products.

Stereochemical memory effects in alkene radical cation/anion contact ion pairs: Effect of substituents, and models for diastereoselectivity

A series of 12 stereochemically defined 2,m-dimethyl- and 2,m,n-trimethyl-6-benzylamino-2-nitro-3-(diphenylphosphatoxy)hexanes have been synthesized and their cyclization reactions leading to di- and trisubstituted N-benzyl pyrrolidines examined in the presence of tributyltin hydride and azoisobutyronitrile in benzene at reflux. The cyclizations are interpreted in terms of generation of an alkyl radical by abstraction of the nitro group with a stannyl radical. The phosphate leaving group is then expelled in a heterolytic cleavage to give a contact alkene radical cation/phosphate anion pair. For the majority of the examples studied, the cyclizations are best understood in terms of nucleophilic attack by the amine on the opposite face of the alkene radical cation to the one shielded by the leaving group, within the confines of the initial contact ion pair, resulting in overall cyclization with inversion of configuration. Dependent on the relative stereochemistry of the substituents, the cyclization is envisaged as taking place through either chair-like or twist-boat-like transition states with the maximum number of substituents pseudo-equatorial. The model breaks down when cyclization on the initial contact ion pair would engender significant destabilizing steric interactions, especially 1,3A strain in the alkene radical cation. In these cases a fully equilibrated Beckwith-Houk-type transition state provides a satisfactory model. Interesting examples of matching and mismatching in the Corey-type oxazaborolidine-mediated reduction of alkyl (methyl-1-nitroethyl) ketones by a β-methyl group in the alkyl chain are reported, and the mismatching is attributed to a developing syn-pentane interaction in the transition state.

Somatostatin analogue compounds

Compounds having somatostatin activity of the following Formula I, 1wherein, R1 is aryl, substituted-aryl, and aryl-(lower-alkyl)-; R2 is lower alkyl, amino substituted lower alkyl, -carboxy-(lower-alkyl), -carbamic acid-(lower-alkyl) and -carboxy-(lower-alkyl)-aryl; and R3 and R4 are independently, lower-alkyl, aryl, substituted-aryl, (substituted-aryl)-(lower-alkyl)-, heteroaryl, (heteroaryl)-(lower-alkyl)-, substituted-heteroaryl, (substituted heteroaryl)-(lower-alkyl)-, heterocyclic, heterocyclic-(lower-alkyl)-, substituted-heterocyclic, (substituted-heterocylic)-(lower alkyl)-, -carboxy-(lower-alkyl), and -carboxy-(lower-alkyl)-aryl; or a pharmaceutically acceptable, ester, ether, or salt thereof; methods for their use; and preparation.

Defining the Molecular Requirements for the Selective Delivery of Polyamine Conjugates into Cells Containing Active Polyamine Transporters

Several N1-substituted polyamines containing various spacer units between nitrogen centers were synthesized as their respective HCl salts. The N1-substituents included benzyl, naphthalen-1-ylmethyl, anthracen-9-ylmethyl, and pyren-1-

Diastereoselectivity in the cyclization of alkene radical cations generated under non-oxidizing conditions: Contact ion pairs and memory effects

A series of highly diastereomerically enriched 1,5-dimethyl-, 2,5-dimethyl-, and 3,5-dimethyl-N-benzyl-5-nitro-4-(diphenylphosphatoxy)hexylamines were exposed to tributyltin hydride and AIBN in benzene at reflux. The ensuing reactions, interpreted in term

Pyrimidinone-1,3-oxathiolane derivatives with antiviral activity

Compounds of formula (I) wherein Ra and Rb the same or different, are hydrogen atoms, acyl groups deriving from a lower carboxylic acid or chains of formula (a) useful as reverse transcriptase inhibitors antiviral activity are described.

Polyamine derivatives as radioprotective agents

The present invention relates to polyamine derivatives of the formula RHN-(CH2)m-NH-(CH2)n-NHR wherein m is an integer from 2 to 4, n is an integer from 3 to 10 and R is C2-C6 alkyl or -(CH2)p-Ar wherein Ar is phenyl or naphthyl and p is an integer from 0

Synthesis and anti-HIV evaluation of new 2',3'-dideoxy-3'-thiacytidine prodrugs

A series of anti-HIV prodrugs possessing various polyaminated side arms have been developed. The incorporation of a N-Boc protected monoamine or diamine side arm into the backbone of the 2',3'-dideoxy-3'-thiacytidine 1 (BCH-189) provided an increase in antiviral potency, which could be several orders magnitude greater than the parent drug (1) depending on the cell culture systems used (MT-4 or MDMs). Twenty six 2',3'-dideoxy-3'-thiacytidine prodrugs which differ from each other by the length, the nature of the 5'-O function and the 5'-O or/and N-4 position on the nucleoside moiety were synthesized. Among this new series of prodrugs, several congeners (12c and 12a) were found to inhibit HIV-1 replication in cell culture with 50% effective concentrations EC50 of 10 and 50 nM respectively, in MT-4 cells. Compound 12c was found more active on infected MDMs cells with 50% effective concentration of 0.01 nM. The synthesis and the antiviral properties of these compounds are discussed.

Method of potentiating cell-mediated immunity utilizing polyamine derivatives

This invention relates to a method of potentiating cell-mediated immunity which comprises administering to a patient a cell-mediated immunity potentiating amount of a compound of the formula: or a pharmaceutically acceptable salt thereof, wherein m is