280-38-6

Usage

Uses

Used in Organic Synthesis:
2-Azabicyclo[2.2.2]octane is used as a building block for the synthesis of complex natural products and pharmaceuticals. Its highly rigid nature and the availability of functionalizable sites make it an ideal candidate for constructing intricate molecular structures.
Used in Pharmaceutical Industry:
2-Azabicyclo[2.2.2]octane is used as a key intermediate in the development of new drugs. Its distinctive reactivity and stability contribute to the creation of novel therapeutic agents with potential applications in various medical fields.
Used in Chemical Research:
2-Azabicyclo[2.2.2]octane is employed as a model compound in academic and industrial research settings. Its unique properties and reactivity provide valuable insights into the study of organic chemistry and the development of new synthetic methodologies.

InChI:InChI=1/C7H13N/c1-3-7-4-2-6(1)5-8-7/h6-8H,1-5H2

Upstream product

• 46410-64-4 2-benzyl-2-aza-bicyclo[2.2.2]octane 
• 62456-15-9 methyl (1s,4s)-4-aminocyclohexane-1-carboxylate 
• 3685-23-2 cis-4-aminocyclohexane-1-carboxylic acid 
• 74403-57-9 2-benzyl-2-aza-bicyclo[2.2.2]octan-3-one 
• 1776-53-0 4-aminocyclohexanecarboxylic acid 
• 3306-69-2 2-aza-bicyclo[2.2.2]octan-3-one 

Downstream Products

• 3693-57-0 2-benzoyl-2-aza-bicyclo[2.2.2]octane 
• 24489-23-4 2-aza-bicyclo[2.2.2]octane-2-carboxylic acid 4-[2-(5-methyl-isoxazole-3-carbonylamino)-ethyl]-benzenesulfonylamide 
• 21744-12-7 2-Nitrosoisoquinuclidine 
• 255863-81-1 (2S)-2-[5-[2-(2-azabicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-N-(2-pyridin-4-ylethyl)propan-1-amine 

Relevant academic research and scientific papers

Piperadinyl-substituted pyridylalkane, alkene and alkine carboxamides

The invention relates to new piperidinyl-substituted pyridyl carboxamides of the general formula (I), wherein the structure element E has meanings (E1) or (E2) and whereby the heterocyclic ring can optionally have a double bond. These substances have especially high cytostatic activities and pronounced immunosuppressive properties which make them suitable for therapeutic treatment in broad tumor spectrum.

An improved preparation of 2-azabicyclo[2.2.2]octane

An improved preparative four-step synthesis to isoquinuclidine tosylate salt 4 has been demonstrated in 70% overall yield from p-aminobenzoic acid (PABA) 1. Hydrogenation of PABA 1 affords 4-aminocyclohexane carboxylic acid 2 as an 80 : 20 mixture of cis- and trans-isomers. Heating the mixture at 250°C effected epimerization and cyclization to provide the bicyclic lactam 3. Subsequent Red-A1 reduction and treatment with tosic acid furnished the desired bicyclic amine, tosylate salt 4.

Benzodiazepine derivatives

Compounds of Formula (I), and salts and prodrugs thereof, wherein R1 represents H, optionally substituted C1-6 alkyl or C3-7 cycloalkyl; R2 is NHR12 or (CH2)s R13 where 5 is 0, 1 or 2; R3 represents C1-6 alkyl, halo or NR6 R7 ; R4 and R5 are H, C1-12 alkyl optionally substituted by NR9 R9' or an azacyclic or azabicyclic group, optionally substituted C4-9 cycloalkyl, C4-9 cycloalkyl C1-4 alkyl, aryl, arylC1-6 alkyl or azacyclic or azabicyclic groups, or R4 and R5 together form the residue of an optionally substituted azacyclic or azabicyclic ring system; x is 0, 1, 2 or 3; R12 is optionally substituted phenyl or pyridyl; R13 represents a group (A) wherein R14 is H or C1-6 alkyl; R15 is H, C1-6 alkyl, halo or NR6 R7 ; and the dotted line is an optional covalent bond; are CCK and/or gastrin antagonists useful in therapy. STR1

PEPTIDE COMPOUNDS DERIVED FROM BORONIC ACID

A compound of formula (I): STR1 in which: R 1 represents hydrogen or acyl, alkyl, benzyl, alkoxycarbonyl, benzyloxycarbonyl, phenoxycarbonyl, 5-[(dimethyl)amino]naphthylsulfonyl, alkoxycarbonylmethyl or carboxymethyl,R 2 represents hydrogen or phenyl, substituted or unsubstituted benzyl, 3-thienylmethyl, 2-pyridylmethyl, diphenylmethyl, fluorenyl, naphthylmethyl, benzocyclobutyl, (dicyclopropylmethyl)methyl, indanyl or (C 3-C 7 cycloalkyl)methyl,R' 2 represents hydrogen or benzylor alternativelyR 2 and R'. sub.2 together represent C 6 H 5--CH=,R. sub.3 represents substituted alkyl or guanidinophenyl, amidinophenyl, aminophenyl, guanidinobenzyl, amidinobenzyl, aminobenzyl or cycloalkyl, R 4 and R 5 each represent hydrogen or alkyl, or STR2 forms a boronic ester of pinanediol, A represents any one of the groups as defined in the description.Medicinal products.

Synthesis of analogues of N (2 chloroethyl) N' trans 4 methylcyclohexyl) N nitrosourea for evaluation as anticancer agents

The superior activity of N (2 chloroethyl) N' (trans 4 methylcyclohexyl) N nitrosourea (MeCCNU) against advanced murine Lewis lung carcinoma in comparisons with the cis form and other nitrosoureas prompted the synthesis of a number of MeCCNU analogues, including several cis trans pairs. The methyl group was replaced by a variety of substituents (CO2H, CH2CO2H, CO2Me, CH2OAc, CH2Cl, OMe); the trans 3 methylcyclohexyl, cis 2 methyl 1,3 dithian 5 yl, cis and trans 2 methyl 1,3 dithian 5 yl tetraoxide, and 1 methylhexyl (open chain) analogues were also prepared. Preliminary tests against murine leukemia L1210 revealed therapeutic indices (ED50/LD10) ranging from 0.26 to 0.79; all but 3 analogues effected 50% cure rates at nontoxic doses, the open chain analogue being one of the least active. In terms of therapeutic index, diequatorial (trans 4) isomers were, with one exception, as active as or, in 4 of the 8 examples, somewhat more active than the corresponding axial equatorial (cis 4) isomers. In this series, 4 of the 5 2-fluoroethyl analogues prepared were clearly inferior to the corresponding 2 chloroethyl analogues.