1699-38-3

Usage

InChI:InChI=1/C15H15ClO2/c1-17-14-8-7-13(10-16)9-15(14)18-11-12-5-3-2-4-6-12/h2-9H,10-11H2,1H3

Upstream product

• 1860-60-2 3-benzyloxy-4-methoxy-benzyl alcohol 
• 100-39-0 benzyl bromide 
• 4383-06-6 3-hydroxy-4-methoxybenzyl alcohol 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 621-59-0 isovanillin 

Downstream Products

• 57535-60-1 3-Benzyloxy-4-methoxybenzylazid 
• 1699-39-4 2-(3-(benzyloxy)-4-methoxyphenyl)acetonitrile 
• 81782-24-3 N-(3-benzyloxy-4-methoxybenzyl)aziridine 
• 6527-13-5 3,4-dimethoxy-(phenylmethoxy)benzaldehyde 
• 221000-98-2 2-(3-Hydroxy-4-methoxy-benzyl)-1-hydroxymethyl-6-methoxy-1,2,3,4-tetrahydro-isoquinolin-7-ol 
• 220935-96-6 1-carbamoyl-2-(3-hydroxy-4-methoxybenzyl)-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 220935-97-7 7-Hydroxy-2-(3-hydroxy-4-methoxy-benzyl)-6-methoxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid methyl ester 
• 220935-95-5 1-cyano-2-(3-benzyloxy-4-methoxybenzyl)-7-benzyloxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 1237514-02-1 1,8-dichloro-[10-(3-benzyloxy-4-methoxyphenylmethyl)]-10H-anthracen-9-one 
• 84293-24-3 N-(3-benzyloxy-4-methoxybenzyl)-N-(2-bromoethyl)-4-benzyloxybenzylamine 
• 84268-57-5 N-(3-benzyloxy-4-methoxybenzyl)-N-(4-benzyloxybenzyl)aminoacetaldehyde 
• 81782-25-4 N-(3-benzyloxy-4-methoxybenzyl)-N-(2-bromoethyl)-4-methoxybenzylamine 
• 81782-27-6 N-(3-benzyloxy-4-methoxybenzyl)-N-(4-methoxybenzyl)aminoacetaldehyde 
• 84268-56-4 N-(3-benzyloxy-4-methoxybenzyl)-N-(2-hydroxyethyl)-4-benzyloxybenzylamine 

Relevant academic research and scientific papers

PHENANTHROINDOLIZIDINE AND PHENANTHROQUINOLIZIDINE ALKALOID HAVING A HYDROXYL GROUP ON THE PHENANTHRENE RING THEREOF, PREPARATION METHOD AND USE THEREOF

A phenanthroindolizidine and phenanthroquinolizidine alkaloid having a hydroxyl group on the phenanthrene ring thereof was synthesized, which exhibits potent activity as an anticancer agent against, such as breast cancer, lung cancer, and prostate cancer.

Designing new analogs for streamlining the structure of cytotoxic lamellarin natural products

Despite the therapeutic potential of marine-derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug-like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully devised to construct a library of 59 systematically designed lamellarin analogs, which were then subjected to cytotoxicity and log P determinations. Along with the 25 first-generation lamellarins previously synthesized in our laboratory, the structure-activity and structure-lipophilicity relationships were extensively evaluated. Our results clearly indicated the additional structural requirements around the lamellarin skeleton which, when combined with those reported previously, can provide invaluable guidance for further modifications to increase the aqueous solubility of these compounds.

Facile and Divergent Synthesis of Lamellarins and Lactam-Containing Derivatives with Improved Drug Likeness and Biological Activities

With the goal to improve the aqueous solubility of lamellarins, the lactone ring in their skeleton was replaced with a lactam moiety in azalamellarins. However, the reported synthetic route produced such derivatives in very low yields. Hence, this study focused on developing an efficient simplified total synthetic scheme that could furnish both azalamellarins and the parent lamellarins from the same pyrrole ester intermediates. Subsequent comparative profiling revealed that the introduced lactone-to-lactam replacement rendered these molecules less lipophilic, whereas their cancer cytotoxicity remained equipotent to that of the parent compounds. Interestingly, their inhibitory activity was significantly enhanced towards the multifaceted GSK-3β enzyme. Our results clearly demonstrate the therapeutic potential of this promising class of marine-derived natural products and justify their further development, especially into anticancer agents.

Discovery of novel 3-benzylquinazolin-4(3H)-ones as potent vasodilative agents

In the present study, a series of 3-benzylquinazolin-4(3H)-ones were synthesized and characterized. Their vasodilative effects were evaluated by wire myograph on isolated rat mesenteric arterial ring induced contraction with 60 mM KCl. The SAR of target compounds was discussed preliminarily. Among these compounds, 2a and 2c displayed potent vasodilatation action and could compete significantly the rat mesenteric arterial rings induced contraction with phenylephrine. Compounds 2a and 2c were further tested for their antihypertensive effects in SHR by oral administration. The results indicated that 2a and 2c could reduce significantly both diastolic and systolic blood pressure. Moreover, 2c displayed antihypertensive effect in a dose dependent manner, and could maintain the effects for 6 h at a dosage of 4.0 mg/kg. These findings suggest that the title compounds are novel vasodilative agents, representing a novel series of promising antihypertensive agents.

NOVEL HYPOXANTHINE AND THIOHYPOXANTHINE COMPOUNDS

Disclosed are compounds of formula (I) wherein R3, R6, R8 are as described herein. The compounds are effective selective PDE IV inhibitors.

Design, synthesis and antiproliferative activity of tripentones: A new series of antitubulin agents

Structure-activity relationship studies of a new series of tripentones (thieno[2,3-b]pyrrolizin-8-ones), led us to prepare several derivatives with antiproliferative activities. The most promising 3-(3-hydroxy-4-methoxyphenyl)thieno[2,3-b]pyrrolizin-8-one 20 (leukemia L1210, IC50 = 15 nM) was shown to be a potent inhibitor of tubulin polymerization.

Design, synthesis, structure-activity relationships, and biological characterization of novel arylalkoxyphenylalkylamine σ ligands as potential antipsychotic drugs

Receptor antagonists may be effective antipsychotic drugs that do not induce motor side effects caused by ingestion of classical drugs such as haloperidol. We obtained evidence that 1-(2-dipropylaminoethyl)-4-methoxy- 6H-dibenzo[b,d]pyran hydrochloride 2a had selective affinity for σ receptor over dopamine D2 receptor. This compound was designed to eliminate two bonds of apomorphine 1 to produce structural flexibility for the nitrogen atom and to bridge two benzene rings with a -CH2O- bond to maintain the planar structure. In light of the evidence, N,Y-dipropyl-2-(4-methoxy-3- benzyloxylphenyl)ethylamine hydrochloride 10b was designed. Since compound 10b had eliminated a biphenyl bond of 6H-dibenzo[b,d]pyran derivative 2a, it might be more released from the rigid structure of apomorphine 1 than compound 2a. The chemical modification of compound 10b led to the discovery that N,N-dipropyl-2-[4-methoxy-3-(2-phenylethoxyl)phenyl]ethylamine hydrochloride 10g (NE- 100), the best compound among arylalkoxyphenylalkylamine derivatives 3, had a high and selective affinity for σ receptor and had a potent activity in an animal model when the drug was given orally. We report here the design, synthesis, structure-activity relationships, and biological characterization of novel arylalkoxyphenylalkylamine derivatives 3.

Photochemical synthesis of 7,8-dioxygenated isoquinoline alkaloids

A new approach to the synthesis of 7,8-dioxygenated tetrahydroisoquinoline alkaloids based on the photo-Fries rearrangement of esters derived from 3-hydroxy-4-methoxy phenylacetonitrile is reported. The procedure was applied to the synthesis of the alkaloid Arizonine and 1-benzyl tetrahydroisoquinoline precursor of cularine and 1,2-berbine alkaloids.

Biosynthesis of the A/B/C/D-Ring System of the Rotenoid Amorphigenin by Amorpha fruticosa Seedlings

With phenylalanine as the starting point, the biosynthesis of the characteristic rotenoid A/B/C/D-ring system of amorphigenin is studied using Amorpha fruticosa seedlings.The course of the biosynthesis can be divided into four phases represented by the bordered and interconnecting Schemes 1, 3, 6 and 7 which summarise the Chalcone-Flavanone Phase, the Flavanone-Isoflavone Phase, the Hydroxylation/Methoxylation Phase and the Rotenoid Phase.By using an INADEQUATE NMR experiment involving the administration of acetate, the type of folding forming ring-D isdemonstrated by 13C-13C coupling and is interpreted as involving a polyketide containing a glutaconate segment which cyclises by a Claisen condensation.The resulting chalcone is cyclised, enzymically and stereospecifically, to 4',7-dihydroxyflavanone.The latter flavanone undergoes aryl migration, in a manner similar to that found in isoflavone biosynthesis, to give 7-hydroxy-4'-methoxyisoflavone.Possible mechanisms for the flavanone-isoflavone rearrangement are discussed, including a proposal that the initiating step involves attack on ring-A and is similar to the first stage of the aromatic hydroxylation of tyrosine to dopa.Although possessing no 4'-hydroxy group in ring-A, the mechanism is also applicable to the recently discovered rotenoids of the Boerhaavia and Iris type, and it provides an explanation for the biogenesis of natural spirobenzocyclobutanes from dihydroeucominoids.Six suitably substituted isoflavonoids labelled with 13C or 3H are synthesized and are used to show that the next hydroxylation (and probably methylation) involves C-3' rather than C-2' in 7-hydroxy-4'-methoxyisoflavone.Whilst the methylations involveS-adenosylmethionine, the hydroxylating enzymes are probably very similar to the flavanone-isoflavone-rearranging enzyme.The closure of ring-B to form finally the rotenoid system probably involves conjugate addition of a methoxyl radical.Prenylation and oxidative modifications are characteristically late-stage processes.