1835-15-0

Usage

Derivative of

Lawsone (a natural dye found in the leaves of the henna plant)

Chemical class

Ketone

Functional groups

Benzyl group
Methoxy group
Hydroxy group
Propanone moiety

Potential applications

Organic synthesis
Pharmaceuticals
Precursor for the synthesis of other compounds

Further investigation needed

To better understand its potential applications in various industries

Upstream product

• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 925-90-6 ethylmagnesium bromide 
• 5438-66-4 1-(4-Benzyloxy-3-methoxy-phenyl)-propan-1-ol 
• 121-33-5 vanillin 
• 100-39-0 benzyl bromide 
• 74-88-4 methyl iodide 
• 1230-59-7 1-benzyloxy-4-(1,2-dibromo-propyl)-2-methoxy-benzene 

Downstream Products

• 7203-54-5 1-(3-Methoxy-4-benzyloxy-phenyl)-2-(2-methoxy-phenoxy)-1-propanon 
• 1774-10-3 (1RS,2SR)-1-(4-hydroxy-3-methoxy-phenyl)-2-(2-methoxy-phenoxy)-propan-1-ol 
• 1835-10-5 (1RS,2SR)-1-(3,4-dimethoxy-phenyl)-2-(2-methoxy-phenoxy)-propan-1-ol 
• 10035-27-5 4,4'-(3,4-dimethylfuran-2,5-diyl)bis(2-methoxyphenol) 
• 61324-71-8 1,4-bis(4-benzyloxy-3-methoxyphenyl)-2,3-dimethylbutane-1,4-dione 
• 61324-72-9 2,5-bis(4-benzyloxy-3-methoxyphenyl)-3,4-dimethylfuran 
• 1835-16-1 1-(4-(benzyloxy)-3-methoxyphenyl)-2-bromopropan-1-one 

Relevant academic research and scientific papers

Structure-activity relationships of talaumidin derivatives: Their neurite-outgrowth promotion in vitro and optic nerve regeneration in vivo

(–)-Talaumidin (1), a 2,5-biaryl-3,4-dimethyltetrahydrofuran lignan, shows potent neurotrophic activities such as neurite-outgrowth promotion and neuroprotection. Previously, we found that (–)-(1S,2R,3S,4R)-stereoisomer 2 exhibited more significant activity than did the natural product talaumidin (1). However, the preparation of optically active (–)-2 requires a complicated synthetic route. To explore new neurotrophic compounds that can be obtained on a large scale, we established a short step synthetic route for talaumidin derivatives and synthesized fourteen analogues based on the structure of (–)-2. First, we synthesized a racemic compound of (–)-2 (2a) and assessed its neurotrophic activity. We found that the neurotrophic property of racemic 2a is similar in activity to that of (–)-2. Using the same synthetic methodology, several talaumidin derivatives were synthesized to optimize the oxy-functionality on aromatic rings. As a result, bis(methylenedioxybenzene) derivative 2b possessed the highest neurotrophic activity. Furthermore, examination of the structure-activity relationships of 2b revealed that the 2,5-diphenyl-tetrahydrofuran structure was an essential structure and that two methyl groups on THF ring could enhance neurotrophic activity. In addition, compounds 2a and 2b were found to induce mouse optic nerve regeneration in vivo.

Efficient Total Synthesis of (±)-Isoguaiacin and (±)-Isogalbulin

1-Arylnaphthalene lignans such as (-)-isoguaiacin and (-)-isogalbulin have been reported to exhibit notable biological properties. While (-)-isoguaiacin has not been previously synthesized, syntheses of (-)-isogalbulin are generally long and produce a mixture of stereoisomers. We herein present the efficient total synthesis of (±)-isoguaiacin and (±)-isogalbulin in seven and eight steps with an overall yield of 46% and 36%, respectively. The reported approach harnesses a hydrogenolysis reaction in acidic conditions, to convert a furan into an arylnaphthalen structure.

COMBINATIONS FOR THE TREATMENT OF PARKINSONISM CONTAINING SELECTIVE NMDA ANTAGONISTS

This invention relates to a method of treating Parkinson's Disease whereby a mammal suffering from Parkinson's Disease is treated with a combination of a forebrain selective NMDA antagonist and a compound which is capable of increasing the excitatory feedback from the ventral lateral nucleus of the thalamus into the cortex. This invention also relates to pharmaceutical compositions containing the synergistic combination.

Neuroprotective 3-(piperidinyl-1)-chroman-4,7-diol and 1-(4-hydroxyphenyl)-2-(piperidinyl-1)-alkanol derivatives

PCT No. PCT/IB95/00380 Sec. 371 Date Feb. 13, 1996 Sec. 102(e) Date Feb. 13, 1996 PCT Filed May 18, 1995 PCT Pub. No. WO96/06081 PCT Pub. Date Feb. 29, 1996This invention relates to compounds of formula (I), or pharmaceutically acceptable acid addition salts thereof, wherein: (a) R2 and R5 are taken separately and R1, R2, R3 and R4 are each independently hydrogen, (C1-C6) alkyl, halo, CF3, OH or OR7 and R5 is methyl or ethyl; or (b) R2 and R5 are taken together, forming a chroman-4-ol ring, and R1, R3 and R4 are each independently hydrogen, (C1-C6) alkyl, halo, CF3, OH or OR7; and R6 is a substituted piperidinyl, pyrrolidinyl or 8-azabicyclo(3.2.1)octanyl derivative; provided that (a) when R2 and R5 are taken separately, at least one of R1, R2, R3 and R4 is not hydrogen; and (b) when R2 and R5 are taken together, at least one of R1, R3 and R4 is not hydrogen; pharmaceutical compositions thereof; and methods of treating mammals suffering from stroke, spinal cord trauma, traumatic brain injury, multiinfarct dementia, CNS degenerative diseases such as Alzheimer's disease, senile dementia of the Alzheimer's type, Huntington's disease, Parkinson's disease, epilepsy, amyotrophic lateral sclerosis, pain, AIDS dementia, psychotic conditions, drug addictions, migraine, hypoglycemia, anxiolytic conditions, urinary incontinence and an ischemic event arising from CNS surgery, open heart surgery or any procedure during which the function of the cardiovascular system is compromised with a compound of formula (I) hereinabove or a pharmaceutically acceptable salt thereof.