106469-57-2

Usage

Uses

Cyanopindolol hemifumarate is a SR-1A/SR-1B antagonist.

Biological Activity

5-HT 1A/1B antagonist with roughly equal affinity at each receptor; also a β -adrenoceptor antagonist.

InChI:InChI=1/2C16H21N3O2.C4H4O4/c2*1-16(2,3)18-9-12(20)10-21-15-6-4-5-14-13(15)7-11(8-17)19-14;5-3(6)1-2-4(7)8/h2*4-7,12,18-20H,9-10H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;;2-1+

Upstream product

• 51336-53-9 4-hydroxy-1H-indole-2-carboxamide 
• 106469-56-1 2-cyano-4-(benzyloxy)indole 
• 39731-09-4 4-benzyloxylindole-2-carboxylic acid 
• 34609-37-5 4-benzyloxy-1H-indole-2-carboxamide 
• 39843-67-9 4-Benzyloxy-1H-indole-2-carbonyl chloride 
• 90-02-8 salicylaldehyde 
• 5896-17-3 2-(phenylmethoxy)benzaldehyde 

Downstream Products

• 126953-42-2 4-(3-{4-[1-(2,4-Dinitro-phenylamino)-1-methyl-ethyl]-1-methyl-cyclohexylamino}-2-hydroxy-propoxy)-1H-indole-2-carbonitrile 
• 106502-44-7 4-{3-[4-(1-Amino-1-methyl-ethyl)-1-methyl-cyclohexylamino]-2-hydroxy-propoxy}-1H-indole-2-carbonitrile 
• 106469-50-5 4-{3-[1-(4-Amino-4-methyl-cyclohexyl)-1-methyl-ethylamino]-2-hydroxy-propoxy}-1H-indole-2-carbonitrile 
• 73907-82-1 4-(2,3-epoxypropoxy)-1H-indol-2-carbonitrile 
• 97730-95-5 DPI 201-106 

Relevant academic research and scientific papers

An efficient synthesis of 4-hydroxy-1H-indole-2-carbonitrile and its conversion to DPI 201-106

A three-step synthesis of 4-hydroxy-1H-indole-2-carbonitrile (3) from commercially available 1,5,6,7-tetrahydro-4H-indol-4-one (4) via cyanation and subsequent halogenation/dehydrohalogenation proceeds in 84% overall yield. The conversion of 3 into positive inotrope DPI 201-106 (1) is also described.

Synthesis of 4-hydroxy-1H-indole-2-carbonitrile via a vinylnitrene cyclization

Literature methods to prepare 1 failed and a reaction sequence was developed to prepare 4-hydroxy-1H-indole-2-carbonitrile (1) by means of an azide decomposition to form the indole ring. The 2-cyano functionality could not be introduced directly but was derived by functionalization of an ester.

Anti-cancer agents and uses thereof

The present invention is in the area of novel compounds and salts thereof, their syntheses, and their use as anti-cancer agents. The compounds include compounds of Formula I: and solvates, hydrates and pharmaceutically-acceptable salts thereof, wherein A1 is N or CR1; A3 is N or CR3; A5 is N or CR5; R1, R3—R6 and L are defined in the specification; n is 0 or 1; and X is an optionally-substituted aryl group having 6-10 carbons in the ring portion, an optionally-substituted 6-membered heteroaryl group having 1-3 nitrogen atoms in the ring portion, an optionally-substituted 5-membered heteroaryl group having 0-4 nitrogen atoms in the ring portion and optionally having 1 sulfur atom or 1 oxygen atom in the ring portion, or an optionally-substituted heteroaryl group in which a 6-membered ring is fused either to a 5-membered ring or to a 6-membered ring, wherein in each case 1, 2, 3 or 4 ring atoms are heteroatoms independently selected from nitrogen, oxygen and sulfur. They are effective against a broad range of cancers, especially leukemia, non-small cell lung and colon.

Affinity Labels for β-Adrenoreceptors: Preparation and Properties of Alkylating β-Blockers Derived from Indole

New alkylating ligands derived from indole with high affinity for β-adrenoceptors were synthesized and their properties examined.N8-(Bromoacetyl)-N1--(Z)-1,8-diamino-p-menthane (8) and its N1,N8 isomer (9) were prepared by the reaction of bromoacetyl bromide with a product of the condensation of 4-indolyl glycidyl ether with (Z)-1,8-diamino-p-menthane.A similar reaction employing 2-cyano-4-indolyl glycidyl ether yielded the respective cyano derivatives 10 and 11.Apparent affinities (Ki, M) for β-adrenoreceptors on membrane preparations from rat heart and lung were 4.6*10-10 and 1.34*10-9 for 8, 2.3*10-8 and 4.5*10-9 for 9, 6.1*10-10 and 1.49*10-9 for 10, and 1.83*10-9 and 2.78*10-9 for 11, respectively.When membranes were preincubated with the above ligands (1*10-8 M, 30 min, 30 deg C) and then washed extensively, reduction in the concentration of specific binding sites of dihydroalprenolol ranged from 7percent to 76percent and there was no change in KD of the remaining binding sites. (+/-)-Alprenolol and (-)-isoproterenol, but not (+)-isoproterenol, when included with the alkylating ligands in the preincubation mixtures, prevented the reduction in concentration of dihydroalprenolol binding sites.Compounds 8-11 alone did not stimulate adenylate cyclase activity in rat heart homogenates.However, these compounds inhibited (-)-isoproterenol-stimulated adenylate cyclase activity with Ki values ranging between 5*10-9 and 60*10-9 M.These results suggest that high-affinity irreversible β-adrenergic antagonists were obtained that may be useful for in vivo studies of β-adrenoceptors.