1860-56-6

Usage

Chemical Properties

Yellow Solid

InChI:InChI=1/C16H15NO4/c1-20-16-11-13(9-10-17(18)19)7-8-15(16)21-12-14-5-3-2-4-6-14/h2-11H,12H2,1H3/b10-9-

Upstream product

• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 75-52-5 nitromethane 
• 100-39-0 benzyl bromide 
• 121-33-5 vanillin 
• 100-44-7 benzyl chloride 
• 60372-07-8 1-(3-methoxy-4-benzyloxyphenyl)-2-nitroethanol 

Downstream Products

• 22231-61-4 2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine 
• 554-52-9 3-Methoxytyramine 
• 35319-99-4 1-benzyloxy-2-methoxy-4-(1-methoxy-2-nitro-ethyl)-benzene 
• 6178-42-3 vanillalnitromethane 
• 1477-68-5 3-Methoxytyramine hydrochloride 
• 2426-89-3 1-benzyloxy-2-methoxy-5-nitro-4-(2-nitrovinyl)benzene 
• 6451-71-4 O,O-Dibenzylscoulerine 
• 6451-70-3 2-(3'-Methoxy-4'-benzyloxy-β-phenethyl)-7-methoxy-8-benzyloxy-1,2,3,4-tetrahydro-3-isoquinolone 
• 791535-84-7 2,9-Bis-benzyloxy-3,10-dimethoxy-5,6,8,13-tetrahydro-isoquino[3,2-a]isoquinolinylium 
• 14383-19-8 (4-ethoxycarbonyloxy-phenyl)-acetic acid-(4-benzyloxy-3-methoxy-phenethylamide) 
• 115293-53-3 (3,4-dimethoxy-2-nitro-phenyl)-acetic acid-(4-benzyloxy-3-methoxy-phenethylamide) 
• 2033-08-1 coclaurine 
• 14383-20-1 carbonic acid ethyl ester-[4-(7-benzyloxy-6-methoxy-3,4-dihydro-[1]isoquinolylmethyl)-phenyl ester] 
• 801171-78-8 1-(7-benzyloxy-6-methoxy-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-4-ethoxycarbonyloxy-benzene 

Relevant academic research and scientific papers

Cactus alkaloids. XXXIII. β-Phenethylamines from the Guatemalan cactus Pilosocereus maxonii

TLC analysis of extracts of Pilosocereus maxonii (Rose) Byles and Rowley detected six identifiable alkaloids. Preparative TLC aided in the crystallization of the hydrochlorides of N-methyl-3,4-dimethoxyphenethylamine, N-methyl-3-methoxytyramine, and N,N-dimethyl-3-methoxytyramine. Traces of 3,4-dimethoxyphenethylamine (TLC and mass spectrometry), tyramine (TLC), and N-methyltyramine (TLC) were identified. While all of these compounds were isolated and/or detected previously in other cactus species this study is the first reported crystallization of N-methyl- and N,N-dimethyl-3-methoxytyramine from a natural source.

C4 phenyl aporphines with selective h5-HT2B receptor affinity

Abstract A group of aporphine alkaloids related to (±)-nantenine (1) and bearing a C4 phenyl and various C1 or N-substituents, was synthesized and evaluated for affinity to h5-HT receptors. In general, unlike nantenine, the analogs lack affinity for the h

Design, synthesis and evaluation of benzo[a]thieno[3,2-g]quinolizines as novel l-SPD derivatives possessing dopamine D1, D2 and serotonin 5-HT1A multiple action profiles

A novel scaffold derived from l-SPD with a substituted thiophene group in the D ring were designed, synthesized, and evaluated for their binding affinities at dopamine (D1, D2 and D3) and serotonin (5-HT1A and 5

Structure–activity relationship and biological evaluation of berberine derivatives as PCSK9 down-regulating agents

Proprotein convertase subtilisin/kexin type 9 (PCSK9) is a secreted protein and its deficiency markedly enhanced the survival rate of patient with cardiovascular diseases (CVDs). Forty berberine (BBR) derivatives were synthesized and evaluated for their activities on down-regulating the transcription of PCSK9 in HepG2 cells, taking BBR as the lead. Structure–activity relationship (SAR) analysis revealed that 2,3-dimethoxy moiety might be beneficial for activity. Among them, 9k displayed the most potent activity with IC50 value of 9.5 ± 0.5 μM, better than that of BBR. Also, it significantly decreased PCSK9 protein level at cellular level, as well as in the liver and serum of mice in vivo. Furthermore, 9k markedly increased LDLR expression and LDL-C clearance via down-regulating PCSK9 protein. The mechanism of action of 9k is targeting HNF1α and/or Sp1 cluster modulation upstream of PCSK9, a different one from BBR. Therefore, 9k might have the potential to be a novel PCSK9 transcriptional inhibitor for the treatment of atherosclerosis, worthy for further investigation.

Full-synthetic method of racemic tetrandrine

The invention discloses a full-synthetic method of racemic tetrandrine, and belongs to the technical field of drug synthesis. The full-synthetic method of the racemic tetrandrine comprises the steps that a synthetic route adopts a convergence synthesis method, a 5-bromovanillin, namely a compound 1 and 3-hydroxy-4-methoxyphenylacetic acid, namely a compound 5 are taken as starting materials to obtain a compound 4 and a compound 6 respectively, then the compound 4 and the compound 6 are taken as raw materials to synthesize a compound 11, a compound 19 is synthesized from the compound 11, and finally, the compound 11 reacts with the compound 19. The full-synthetic method of the racemic tetrandrine has the advantages that the synthetic efficiency is higher, the yield is higher, and the cost is lower; the reaction conditions are milder, the operation is simple and convenient, the industrial value is higher, and a reference is provided for the full-synthetic method of optical voidness tetrandrine.

Benzo aza compound, preparation method and use thereof

Belonging to the field of pharmaceutical chemistry, the invention relates to a benzoazepine compound, a preparation method and application thereof, in particular to the benzoazepine compound, its preparation method and application in the field of treatment of nervous system diseases, especially application in the field of drug addiction related to dopamine D1 and D3 receptors. The benzoazepine compound and pharmacologically acceptable inorganic or organic salts thereof have a structure shown as formula (I). Results of drug experiments carried out by the invention show that the benzoazepine compound and its pharmacologically acceptable inorganic or organic salts have high antagonistic activity on dopamine D1 and D3, can be used as drug leads for further development of dopamine receptor antagonists with good selectivity and high activity, and can be used as potential drugs for treatment of drug addiction by dopamine D1, D3 receptor antagonists. (formula (I)).

Asymmetric total synthesis of tetrahydroprotoberberine derivatives and evaluation of their binding affinities at dopamine receptors

Cocaine addiction remains a serious challenge for clinical and medical research because there is no effective pharmacological treatment. L-THP, a natural product isolated from Corydalis yanhusuo W.T. Wang, is one of the most frequently used traditional herbs to treat drug addiction in China. Our laboratory first reported that its demethylated metabolites L-ICP, L-CD, and L-CP had high affinity at dopamine D1, D2, and D5 receptors. Here we report the chemical synthesis of these metabolites and other derivatives and their binding affinities at dopamine receptors. The synthesis of these bioactive metabolites will allow further in vivo study of their potential in treating cocaine addiction.

ZrCl4-mediated synthesis of 1,2,3-triazoles from vinyl nitrates and their biological evaluation

A ZrCl4-mediated simple method for the conversion of vinyl nitrates to 1,2,3-triazoles in excellent yields is developed. The obtained new triazoles were evaluated for their antimicrobial activity.

Functional reversal of (?)-Stepholidine analogues by replacement of benzazepine substructure using the ring-expansion strategy

(?)-Stepholidine is an active ingredient of the Chinese herb Stephania and naturally occurring tetrahydroprotoberberine alkaloid with mixed dopamine receptor D1 agonistic and dopamine receptor D2 antagonistic activities. In this work, a series of novel hexahydrobenzo[4,5]azepino [2,1-a]isoquinolines were designed and synthesized as ring-expanded analogues of (?)-Stepholidine. Initial pharmacological assays demonstrated that a benzazepine replacement was associated with significant increase in selectivity and functional reversal at dopamine receptor D1. Compound-(?)-15e (Ki?=?5.32?±?0.01?nm) is more potent than (?)-Stepholidine (Ki?=?13?nm) and was identified as a selective dopamine receptor D1 antagonist (IC50?=?0.14?μm). Moreover, molecular modeling suggested that (?)-15e might exert its dopamine receptor D1 antagonistic activities through interacting with the transmembrane helix 7 of dopamine receptor D1.

N-METHYL-D-ASPARTATE RECEPTOR (NMDAR) POTENTIATORS, PHARMACEUTICAL COMPOSITIONS, AND USES RELATED THERETO

This disclosure relates to tetrahydroisoquinolines, salts, and derivatives useful for managing mental or cognitive diseases or conditions of the brain or central nervous system. In certain embodiments, the disclosure relates to compounds and compositions