10538-48-4

Usage

Uses

Used in Pharmaceutical Industry:
3-(2,3-DIMETHOXYPHENYL)PROPANOIC ACID is used as a key intermediate compound for the synthesis of 5-HT2c receptor agonists, which are biologically active compounds. These agonists play a crucial role in modulating various physiological processes and have potential therapeutic applications in treating a range of disorders, including mood and anxiety disorders, as well as certain neurological conditions.
The synthesis of 5-HT2c receptor agonists from 3-(2,3-DIMETHOXYPHENYL)PROPANOIC ACID involves a series of chemical reactions that exploit the compound's reactivity and functional groups. The end products, once synthesized, can be subjected to further testing and optimization to enhance their efficacy, selectivity, and safety profile for use in clinical settings.

InChI:InChI=1/C11H14O4/c1-14-9-5-3-4-8(11(9)15-2)6-7-10(12)13/h3-5H,6-7H2,1-2H3,(H,12,13)/p-1

Upstream product

• 7461-60-1 2,3-dimethoxycinnamic acid 
• 7345-82-6 trans-2,3-dimethoxycinnamic acid 
• 38489-68-8 2,3-dimethoxy-cis-cinnamic acid 
• 86-51-1 2,3-dimethyoxybenzaldehyde 

Downstream Products

• 63307-15-3 4-(2,3-Dimethoxy-phenyl)-1-methanesulfinyl-butan-2-one 
• 103853-10-7 3-(2,3-dimethoxyphenyl)propan-1-ol 
• 88387-97-7 3-(2,3-Dimethoxy-phenyl)-propionyl azide 
• 106800-28-6 3-(2-hydroxy-3-methoxyphenyl)propanol 
• 106800-29-7 3-(3-hydroxy-2-methoxyphenyl)propanol 
• 1378239-14-5 6-methoxy-3-(3',4',5'-trimethoxyphenyl)-1H-inden-7-ol 

Relevant academic research and scientific papers

BENZOSUBERENE ANALOGUES AND RELATED COMPOUNDS WITH ACTIVITY AS ANTICANCER AGENTS

A series of benzosuberene analogues demonstrate effective inhibition of tubulin polymerization, cytotoxicity against human cancer cell lines, and vascular disruption in tumors.

Structure Guided Design, Synthesis, and Biological Evaluation of Novel Benzosuberene Analogues as Inhibitors of Tubulin Polymerization

A promising design paradigm for small-molecule inhibitors of tubulin polymerization that bind to the colchicine site draws structural inspiration from the natural products colchicine and combretastatin A-4 (CA4). Our previous studies with benzocycloalkeny

BENZOCYCLOOCTENE-BASED AND INDENE-BASED ANTICANCER AGENTS

Benzocyclooctene (fused 6,8 ring system) analogues and corresponding indene (fused 6,5 ring system) analogues function as inhibitors of tubulin polymerization. The compounds are useful as anticancer agents in a new therapeutic approach for cancer treatment utilizing small-molecule inhibitors of tubulin polymerization that also act as vascular disrupting agents (VDAs).

Synthesis and biological evaluation of benzocyclooctene-based and indene-based anticancer agents that function as inhibitors of tubulin polymerization

The natural products colchicine and combretastatin A-4 (CA4) have been inspirational for the design and synthesis of structurally related analogues and spin-off compounds as inhibitors of tubulin polymerization. The discovery that a water-soluble phosphate prodrug salt of CA4 (referred to as CA4P) is capable of imparting profound and selective damage to tumor-associated blood vessels paved the way for the development of a new therapeutic approach for cancer treatment utilizing small-molecule inhibitors of tubulin polymerization that also act as vascular disrupting agents (VDAs). Combination of salient structural features associated with colchicine and CA4 led to the design and synthesis of a variety of fused aryl-cycloalkyl and aryl-heterocyclic compounds that function as inhibitors of tubulin polymerization. Prominent among these compounds is a benzosuberene analogue (referred to as KGP18), which demonstrates sub-nM cytotoxicity against human cancer cell lines and functions (when administered as a water-soluble prodrug salt) as a VDA in mouse models. Structure activity relationship considerations led to the evaluation of benzocyclooctyl [6,8 fused] and indene [6,5 fused] ring systems. Four benzocyclooctene and four indene analogues were prepared and evaluated biologically. Three of the benzocyclooctene analogues were active as inhibitors of tubulin polymerization (IC50 50 = 11 μM) with reduced potency. The most potent inhibitor of tubulin polymerization from this group was benzocyclooctene analogue 23, and it was converted to its water-soluble prodrug salt 24 to assess its potential as a VDA. Preliminary in vivo studies, which utilized the MCF7-luc-GFP-mCherry breast tumor in a SCID mouse model, demonstrated that treatment with 24 (120 mg kg?1) resulted in significant vascular shutdown, as evidenced by bioluminescence imaging at 4 h post administration, and that the effect continued at both 24 and 48 h. Contemporaneous studies with CA4P, a clinically relevant VDA, were carried out as a positive control.

Elucidation of a structural basis for the inhibitor-driven, p62 (SQSTM1)-dependent intracellular redistribution of cAMP phosphodiesterase-4A4 (PDE4A4)

Figure Presented. A survey of PDE4 inhibitors reveals that some compounds trigger intracellular aggregation of PDE4A4 into accretion foci through association with the ubiquitin-binding scaffold protein p62 (SQSTM1). We show that this effect is driven by i

Derivatives of azetidine and pyrrolidine

The invention relates to a compound having formula (I) wherein A is an optionally unsaturated 5- or 6-membered ring, which may comprise a heteroatom selected from N, O and S and which may be substituted with oxo or (1-6C)alkyl; R1, R2and R3are independently H, (1-6C)alkyl, (1-6C)alkoxy, (1-6C)alkoxy(1-6C)-alkyl, carbo(1-6C)alkoxy or halogen; X is O or S; and n is 1 or 2; or a pharmaceutically acceptable salt thereof, with the exception of 3-(naphth-1-yl-oxy)-pyrolidin and 3-(5,6,7,8-tetmhydro-naphth-1-yl-oxy)-pyrolidin. The compounds of the invention have antidepressant activity and can be used in treating or preventing serotonin-related diseases.

Efficient synthesis of the 5-HT2C receptor agonist, Org 37684

An efficient synthesis of the 5-HT2C receptor agonist Org 37684 is presented. The synthesis utilises the regioselective demethylation of an arylether as the key step.

Derivatives of azetidine and pyrrolidine

The invention relates to a compound having the formula I wherein A is an optionally unsaturated 5- or 6-membered ring, which may comprise a heteroatom selected from N, O and S and which may be substituted with oxo or (1-6C)alkyl; R1, R2and R3are independently H, (1-6C)alkyl, (1-6C)alkoxy, (1-6C)alkoxy-(1-6C)alkyl, carbo(1-6C)alkoxy or halogen; X is O or S; and n is 1 or 2; or a pharmaceutically acceptable salt thereof, with the exception of 3-(naphth-1-yl-oxy)-pyrrolidin and 3-(5,6,7,8-tetrahydro-naphth-1-yl-oxy)-pyrrolidin., The compounds of the invention have antidepressant activity and can be used in treating or preventing serotonin-related diseases.

Synthesis and pharmacological evaluation of 5,6,7,8-tetrahydro-6-amino>-1,2-naphthalenediol: a novel non-selective dopamine-receptor agonist

Based on the hypothesis that simultaneous stimulation of dopamine-D1 and -D2 receptors could be beneficial for the treatment of Parkinson's disease, we prepared 5,6,7,8-tetrahydro-6-amino>-1,2-naphthalenedi

Tyrphostins. 2. Heterocyclic and α-Substituted Benzylidenemalonitrile Tyrphostins as Potent Inhibitors of EGF Receptor and ErbB2/neu Tyrosine Kinases

We have previously described a novel series of low molecular weight protein tyrosine kinase inhibitors which we named tyrphostins.The characteristic active pharmacophore of these compounds was the hydroxy-cis-benzylidenemalonitrile moiety.In this article we describe three novel groups of tyrphostins: (i) one group has the phenolic moiety of the cis-benzylidenemalononitrile replaced either with other substituted benzenes or with heteroaromatic rings, (ii) another is a series of conformationally constrained derivatives of hydroxy-cis-benzylidenemalononitriles in which the malononitrile moiety is fixed relative to the aromatic ring, and (iii) two groups of compounds in which the position trans to the benzenemalononitrile has been substituted by ketones and amides.Among the novel tyrphostins examined we found inhibitors which discriminate between the highly homologous EGF receptor kinase (HER1) and ErbB2/neu kinase (HER2).These findings may lead to selective tyrosine kinase blockers for the treatment of diseases in which ErbB2/neu is involved.