194151-99-0

Usage

InChI:InChI=1/C9H11NO/c11-9-5-1-4-8-7(9)3-2-6-10-8/h2-3,6,9,11H,1,4-5H2

Upstream product

• 53400-41-2 5,6,7,8-tetrahydroquinolin-5-one 
• 5220-49-5 3-amino-cyclohex-2-enone 

Downstream Products

• 198401-82-0 5-chloro-5,6,7,8-tetrahydroquinoline 
• 1417346-96-3 C₂₈H₃₂ClN₅O₄ 
• 98218-77-0 (Z)-2-Phenyl-3,3a,4,5,6,9,10,11-octahydro-2H-1-oxa-11a-aza-cyclopentacyclodecene 
• 98218-73-6 3-[(4aS,5R,8aS)-5-(Toluene-4-sulfonyloxy)-octahydro-quinolin-1-yl]-propionic acid methyl ester 
• 98218-74-7 1-hydroxy-cis,cis-5-<(p-tolylsulfonyl)oxy>decahydroquinoline 
• 137491-99-7 5,6-Epoxy-5,6,7,8-tetrahydroquinoline 
• 87707-14-0 1a,7b-dihydrooxireno[2,3-f]quinoline 

Relevant academic research and scientific papers

Switchable Regioselective 6-endo or 5-exo Radical Cyclization via Photoredox Catalysis

Controlling the regioselectivity of radical cyclizations to favor the 6-endo mode over its kinetically preferred 5-exo counterpart is difficult without introducing substrate prefunctionalization. To address this challenge, we have developed a simple method for reagent controlled regioselective radical cyclization of halogenated N-heterocycles onto pendant olefins. Radical generation occurs under mild photoredox conditions with control of the regioselectivity governed by the rate of hydrogen atom transfer (HAT). Utilizing a polarity-matched thiol-based HAT agent promotes the highly selective formation of the 5-exo cyclization product. Conversely, limiting the solubility of the HAT reagent Hantzsch ester (HEH) leads to selective formation of the thermodynamically favored 6-endo product. This occurs through an initial 5-exo cyclization, with the resulting alkyl radical intermediate undergoing neophyl rearrangement to form the 6-endo product. Development of this switchable catalysis strategy allows for two modes of divergent reactivity to form either the 6-endo or 5-exo product, generating fused N-heteroaromatic/saturated ring systems.

WDR5 INHIBITORS AND MODULATORS

Isoquinolmone compounds and derivatives inhibit WDR5 and associated protein-protein interactions, and the compounds and their pharmaceutical compositions are useful for treating disorders and conditions in a subject, such as cancer cell proliferation.

Cyclic gyrase and topoisomerase IV inhibitor

The invention belongs to the technical field of medicament, and particularly relates to a compound shown in formula (I) (please see the formula (I) in the description), and acceptable salt, ester or stereoisomer of the compound in pharmacy. R1, R2, a ring

1-Imidazolylcarbonyloxy-substituted tetrahydroquinolines and pyridines: Synthesis and evaluation of P450 TxA2 inhibition

The title compounds are derived from our model describing structural requirements for strong P450 TxA2 inhibition. In the present paper the syntheses of the 1-imidazolylcarbonyloxy-substituted tetrahydroquinolines 1, 3, and 4, tetrahydro-naphthalene 2 and 3-ethylpyridines 5 and 6 are described. Using our P450 TxA2 inhibition assay, 1-6 were tested for enzyme inhibitory activity. Compound 1 (5-(1-imidazolylcarbonyloxy)-5,6,7,8- tetrahydroquinoline) turned out to be the most active derivative showing a potency similar to the reference compound dazoxiben (IC50 values 1.6 and 1.1 μM).

Development of orally active oxytocin antagonists: Studies on 1-(1-{4- [1-(2-methyl-1-oxidopyridin-3-ylmethyl)piperidin-4-yloxy].2methoxybenzoyl}- 4-yl)-1,4-dihydrobenz[d][1,3]oxazin-2-one (L-372,662) and related pyridines

The previously reported oxytocin antagonist L-371,257 (2) has been modified at its acetylpiperidine terminus to incorporate various pyridine N- oxide groups. This modification has led to the identification of compounds with improved pharmacokinetics and excellent oral bioavailability. The pyridine N-oxide series is exemplified by L-372,662 (30), which possessed good potency in vitro (Ki = 4.1 nM, cloned human oxytocin receptor) and in vivo (intravenous AD50 = 0.71 mg/kg in the rat), excellent oral bioavailability (90% in the rat, 96% in the dog), good aqueous solubility (>8.5 mg/mL at pH 5.2) which should facilitate formulation for iv administration, and excellent selectivity against the human arginine vasopressin receptors. Incorporation of a 5-fluoro substituent on the central benzoyl ring of this class of oxytocin antagonists enhanced in vitro and in vivo potency but was detrimental to the pharmacokinetic profiles of these compounds. Although lipophilic substitution around the pyridine ring of compound 30 gave higher affinity in vitro, such substituents were a metabolic liability and caused shortfalls in vivo. Two approaches to prevent this metabolism, addition of a cyclic constraint and incorporation of trifluoromethyl groups, were examined. The former approach was ineffective because of metabolic hydroxylation on the constrained ring system, whereas the latter showed improvement in plasma pharmacokinetics in some cases.

TOCOLYTIC OXYTOCIN RECEPTOR ANTAGONISTS

This invention relates to certain novel benzoxazinone compounds and derivatives thereof, their synthesis, and their use as oxytocin receptor antagonists. One application of these compounds is in the treatment of preterm labor. The ability of the compounds to relax uterine contractions in mammals also makes them useful for treating dysmenorrhea and stopping labor prior to cesarean delivery. A typical compound is as follows: STR1

Nitrones by Heterolytic Fragmentation of γ-N-Hydroxyamino Sulfonates. Conversion of a Decahydroquinoline to a Perhydroazaazulene

(E,Z)-1-Azacyclodeca-1,6-diene 1-oxide (4) was generated by fragmentation of 1-hydroxy-cis,cis-5-decahydroquinoline (3a) under basic conditions.The nitrone 4 underwent in situ intramolecular cycloaddition to a 1-aza-11-oxatricyclo5.