Benzopyran

About: Benzopyran is a research topic. Over the lifetime, 1889 publications have been published within this topic receiving 15235 citations.

Pyranoquinolines and their use as pharmaceuticals

Abstract: Pharmaceutical compounds of the formula R is phenyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl and heteroaryl groups being optionally substituted, or R is furanyl optionally substituted with C1-4 alkyl; R is nitrile, carboxy, -COOR where R is an ester group, -CONR R where R and R are each hydrogen or C1-4 alkyl, or R SO2- where R is C1-4 alkyl or optionally substituted phenyl; R is -NR R , -NHCOR , -N(COR )2, -N=CHOR where R and R are each hydrogen or C1-4 alkyl, or -NHSO2R where R is C1-4 alkyl or optionally substituted phenyl; or where X is C2-4 alkylene; and the group represents a pyridine ring fused to the benzopyran nucleus; and salts thereof.

Synthesis and σ receptor affinity of spiro[[2]benzopyran-1,1'-cyclohexanes] with an exocyclic amino moiety in the 3'-position.

Abstract: The main functions of σ1 receptors include the modulation of release and reuptake of neurotransmitters, the regulation of ion channels and the influence on intracellular signaling through modulation of calcium levels. Due to these properties, σ1 receptors are interesting drug targets for the treatment of various neurological disorders, pain and cancer. In order to modify the distance between the pharmacophoric elements (the benzene ring of 2-benzopyran and an amino moiety), a set of spiro[[2]benzopyran-1,1′-cyclohexan]-3′-amines was synthesized. The key step of the synthesis was a Parham cyclization of 1-bromo-2-(2-bromoethyl)benzene (6) with the mono ketal 7 of cyclohexane-1,3-dione, which led in a one-pot reaction to the spirocyclic framework 8. Reductive amination of ketone 9 stereoselectively provided secondary amines cis-4, which were methylated to afford tertiary amines cis-5. Whereas spirocyclic compounds cis-4a and cis-5a bearing a benzyl moiety at the exocyclic amino moiety showed rather low σ1 affinity, the corresponding cyclohexylmethyl derivatives cis-4b and cis-5b exhibited low nanomolar σ1 affinity. The secondary amine cis-4b displayed the highest σ1 receptor affinity (Ki = 5.4 nM) in this series. Methylation of the secondary amine cis-4b led to a slightly decreased σ1 receptor affinity of cis-5b (Ki = 15 nM).

Tricyclic benzopyrane compound

Abstract: This invention relates to benzopyran derivatives of formula (I) or (II), or pharmaceutically acceptable salts thereof wherein R 1 and R 2 are independently of each other hydrogen atom, C 1-6 alkyl group or C 6-14 aryl group, R 3 is hydrogen atom or C 1-6 alkylcarbonyloxy group, or together with R 4 forms a bond, R 4 is hydrogen atom, or together with R 3 forms a bond, m is an integer of 0 to 4, n is an integer of 0 to 4, V is a single bond, CR 7 R 8 , NR 9 , O, S, SO or SO 2 , R 5 is hydrogen atom or C 1-6 alkyl group, R 6 is hydrogen atom, C 1-6 alkyl group, C 3-8 cycloalkyl group, C 3-8 cycloalkenyl group, amino group, C 1-6 alkylamino group, di-C 1-6 alkylamino group, C 6-14 arylamino group, C 2-9 heteroarylamino group, C 6-14 aryl group, C 2-9 heteroaryl group or C 2-9 heterocyclyl group, A is 5-, 6- or 7-member ring fused with benzene ring, as constituent atom of the ring, oxygen atom, nitrogen atom or sulfur atom may be contained in the number of 1 to 3 alone or in a combination thereof, the number of unsaturated bond in the ring is 1, 2 or 3 including an unsaturated bond of the benzene ring to be fused, carbon atoms constituting the ring may be carbonyl or thiocarbonyl. These compounds are useful as an anti-arrhythmic agent.

Crystal structure of prop-2-en-1-yl 2-oxo-2H-1-benzopyran-3-carboxylate, C13H10O4

Abstract: Abstract C13H10O4, monoclinic, P21/n (no. 14), a = 9.3751(2) Å, b = 17.3340(3) Å, c = 13.3828(2) Å, β = 98.460(1)°, V = 2151.15(7) Å3, Z = 8, Rgt(F) = 0.0381, wRref(F2) = 0.1065, T = 150(2) K.