865712-55-6

Basic information

• Product Name: (R)-2-(2-tert-butoxycarbonylamino-2-cyclohexylethoxy)-bromobenzene
• Synonyms: (R)-2-(2-tert-butoxycarbonylamino-2-cyclohexylethoxy)-bromobenzene
• CAS NO: 865712-55-6
• Molecular Weight: 398.34
• Mol File: 865712-55-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R)-2-(2-tert-butoxycarbonylamino-2-cyclohexylethoxy)-bromobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(2-tert-butoxycarbonylamino-2-cyclohexylethoxy)-bromobenzene(865712-55-6)
• EPA Substance Registry System: (R)-2-(2-tert-butoxycarbonylamino-2-cyclohexylethoxy)-bromobenzene(865712-55-6)

Safety Data

• Hazardous Substances Data: 865712-55-6(Hazardous Substances Data)

Upstream product

• 95-56-7 2-hydroxybromobenzene 
• 188348-00-7 (R)-1-(cyclohexyl-2-hydroxyethyl)carbamic acid tert-butyl ester 

Downstream Products

• 856703-19-0 (R)-4-tert-butoxycarbonyl-3-cyclo-hexyl-3, 4-dihydro-2H-1, 4-benzoxazine 

Relevant articles and documents

Design, synthesis, and structure-activity relationship study of conformationally constrained analogs of indole-3-carboxamides as novel CB1 cannabinoid receptor agonists

Novel tricyclic indole-3-carboxamides were synthesized as structurally restricted analogs of bicyclic indoles, and found to be potent CB1 cannabinoid receptor agonists. The CB1 agonist activity depended on the absolute configuration of the chiral center of the tricyclic ring. The preferred enantiomer was more potent than the structurally unconstrained lead compound. Structure-activity relationships in the amide side chain of the indole C-3 position were also investigated.

(INDOL-3-YL)-HETEROCYCLE DERIVATIVES AS AGONISTS OF THE CANNABINOID CB1 RECEPTOR

The invention relates to (indol-3-yl)-heterocycle derivatives having general Formula (I) wherein A represents a 5-membered aromatic heterocyclic ring, wherein X1, X2 and X3 are independently selected from N, O, S and CR; R is H or (C1-4)alkyl; or R, when present in X2 or X3, may form together with R3 a 5-8 membered ring; R1 is a 5-8 mem-bered saturated carbocyclic ring, optionally containing a heteroatom selected from O and S; R2 is H, CH3 or CH2-CH3;or R2 is joined together with R7 to form a 6-mem-bered ring, optionally containing a heteroatom selected from O and S, and which heteroatom is bonded to the 7-position of the indole ring; R3 and R4 are independent-ly H, (C1-6)alkyl or (C3-7)cycloalkyl, the alkyl groups being optionally substituted with OH, (C1-4)alkyloxy, (C1-4)alkylthio, (C1-4)alkylsulfonyl, CN or halogen; or R3 together with R4 and the N to which they are bonded form a 4-8 membered ring optionally containing a further heteroatom selected from O and S, and which is optionally sub-stituted with OH, (C1-4)alkyl, (C1-4)alkyloxy, (C1-4)alkyloxy- (C1-4)alkyl, or halogen; or R3 together with R5 forms a 4-8 membered ring optionally containing a further hetero-atom selected from O and S, and which is optionally substituted with OH, (C1-4)alkyl, (C1-4)alkyloxy, (C1-4)alkyloxy- (C1-4)alkyl, or halogen; or R3 together with R, when present in X2 or X3, forms a 5-8 membered ring; R5 is H or (C1-4)alkyl; or R5 together with R3 forms a 4-8 membered ring optionally containing a further heteroatom select-ed from O and S, and which is optionally substituted with OH, (C1-4)alkyl, (C1-4)alkyl-oxy, (C1-4) alkyloxy- (C1-4)alkyl, or halogen; R5' is H or (C1-4)alkyl; R6 represents 1-3 substituents independently selected from H, (C1-4 alkyl, (C1-4) alkyloxy, CN and halogen; R7 is H, (C1-4)alkyl, (C1-4)alkyloxy, CN or halogen; or R7 is joined together with R2 to form a 6-membered ring, optionally containing a further heteroatom selected from O and S, and which heteroatom is bonded to the 7-position of the indole ring; or a pharmaceutically acceptable salt thereof, as agonists of the cannabinoid CB1 receptor, which can be used in the treatment of pain such as for example peri-operative pain, chronic pain, neuropathic pain, cancer pain and pain and spasticity associated with multiple sclerosis.