6522-02-7

Usage

Chemical class

Carboxylic acid

Functional group

Allyloxy group

Structure

Phenyl ring with allyloxy group attached

Common uses

Starting material in organic synthesis, building block for pharmaceuticals and agrochemicals

Properties

Valuable for drug development, diverse chemical reactivity, potential applications in materials science and industrial chemistry

InChI:InChI=1/C16H17N3OS2/c1-3-19-15(20)14(22-16(19)21)11-12-5-7-13(8-6-12)18(2)10-4-9-17/h5-8,11H,3-4,10H2,1-2H3

Upstream product

• 6522-01-6 methyl 3-(4-allyloxyphenyl)propanoate 
• 5597-50-2 3-(4-hydroxyphenyl)propionic acid methyl ester 
• 106-95-6 allyl bromide 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 872209-97-7 C₁₃H₁₄O₅ 
• 7400-08-0 p-Coumaric Acid 

Downstream Products

• 515835-01-5 3-(4-allyloxy-phenyl)-propionic acid hex-5-enyl ester 
• 1610043-23-6 ethyl 5-(3-(4-(allyloxy)phenyl)propanoyl)-1H-pyrrole-2-carboxylate 
• 1610042-98-2 (S)-2,13-dioxo-N-((S)-1-oxo-3-phenylpropan-2-yl)-1¹H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxamide 
• 1610043-18-9 (S)-N-((S)-1-hydroxy-3-phenylpropan-2-yl)-2,13-dioxo-11H-6-oxa-12-aza-1(2,5)-pyrrola-5(1,4)-benzenacyclotridecaphane-11-carboxamide 
• 1610043-28-1 methyl (2S)-3-(4-allyloxyphenyl)-2-[[5-[3-(4-allyloxyphenyl)propanoyl]-1H-pyrrole-2-carbonyl]amino]propanoate 
• 1610043-27-0 methyl (2S)-2-[[5-[3-(4-allyloxyphenyl)propanoyl]-1H-pyrrole-2-carbonyl]amino]pent-4-enoate 
• 1610043-25-8 5-(3-(4-(allyloxy)phenyl)propanoyl)-1H-pyrrole-2-carboxylic acid 

Relevant academic research and scientific papers

TRUNCATED ITRACONAZOLE ANALOGUES AND METHODS OF USE THEREOF

Disclosed herein are analogues of itraconazole that are potent hedgehog signaling pathway inhibitors. The compounds are expected to be useful in the treatment of cell proliferation disorders such as cancer, particularly cancers that are dependent upon the hedgehog signaling pathway such as basal cell carcinoma and medulloblastoma.

Truncated Itraconazole Analogues Exhibiting Potent Anti-Hedgehog Activity and Improved Drug-like Properties

We conducted a structure-activity relationship study to explore simplified analogues of the itraconazole (ITZ) scaffold for their ability to inhibit the hedgehog (Hh) signaling pathway. These analogues were based on exploring the effects of chemical modifications to the linker and triazolone/side chain region of ITZ. Analogue 11 was identified as the most potent compound in our first generation, with an IC50 value of 81 nM in a murine Hh-dependent basal cell carcinoma. Metabolic identification studies led us to identify truncated piperazine (26) as the major metabolite in human liver microsomes (HLMs) and an improved Hh pathway inhibitor (IC50 = 22 nM). This work verifies that continued truncation of the ITZ scaffold is a practical method to maintain potent anti-Hh activity while also reducing the molecular weight for the ITZ scaffold and achieving improved pharmacokinetic properties.

Synthesis of Albicidin Derivatives: Assessing the Role of N-terminal Acylation on the Antibacterial Activity

The peptide antibiotic albicidin, which is synthesized by the plant pathogenic bacterium, Xanthomonas albilineans, represents the most prominent member of a new class of antibacterial gyrase inhibitors. It shows remarkable antibacterial activities against Gram-positive and Gram-negative microorganisms. Its unique structure potentially represents a new lead structure for the development of an antibacterial drug. Here we report the synthesis of 14 albicidin derivatives with structural variations at the N-terminus, primarily investigating the effects of variation of cinnamoyl, phenylpropanoyl, and benzoyl residues. Gyrase inhibition in vitro and determination of minimal inhibitory concentrations were assessed in parallel. Activities in a nanomolar range and the importance of N-acylation were demonstrated.

MACROCYCLIC COMPOUNDS AND USES THEREOF

The present invention relates to novel macrocyclic compounds of Formula I and their use as novel therapeutic agents for example as novel compounds used in methods of preventing and/or treating a disease, condition or state in a subject associated with dysregulation of protease activity and/or dysregulation of proteosome activity

Macrocyclic protease inhibitors with reduced peptide character

There is a real need for simple structures that define a β-strand conformation, a secondary structure that is central to peptide-protein interactions. For example, protease substrates and inhibitors almost universally adopt this geometry on active site binding. A planar pyrrole is used to replace two amino acids of a peptide backbone to generate a simple macrocycle that retains the required geometry for active site binding. The resulting β-strand templates have reduced peptide character and provide potent protease inhibitors with the attachment of an appropriate amino aldehyde to the C-terminus. Picomolar inhibitors of cathepsin L and S are reported and the mode of binding of one example to the model protease chymotrypsin is defined by X-ray crystallography. The incorporation of a pyrrole into a peptide backbone generates simple macrocycles that adopt a β-strand geometry. The attachment of a P1 amino aldehyde to these templates then gives rise to potent protease inhibitors (see example, top, which has Ki values of 440 pM and 920 pM against the cysteine cathepsins L and S, respectively). A crystal structure of a related derivative bound to chymotrypsin (see picture, bottom) confirms the design.

Toll-like receptor 2 antagonists. Part 1: Preliminary SAR investigation of novel synthetic phospholipids

Novel synthetic phospholipid compound 1 was discovered to be an antagonist of human toll-like receptor 2 (TLR2) signaling. In a preliminary SAR campaign we synthesized several analogues of 1 and found that considerable structural changes could be made wit

Synthetic approach to pondaplin and highly strained ansa macrolides: The dramatic influence of a fluorine atom on the efficiency of ring-closing metathesis

Ring-closing metathesis has been applied to the synthesis of extremely rigid 13 to 16 membered ring lactones starting from alkenyl p-(O-allyl)cinnamates and p-(O-allyl)dihydrocinnamates. The core structure of pondaplin, a natural ansa macrolide has been prepared starting from a fluoro derivative. The presence of this atom seems to have a crucial role on the success of the RCM.

Enediyne derivatives useful for the synthesis of conjugates of methyltrithio antitumor agents

This invention describes carrier-drug conjugates prepared from disulfide analogs of the calicheamicin family of potent antitumor antibiotics and their derivatives, as well as similar analogs from related antitumor antibiotics such as the esperamicins. The carrier can be an antibody, growth factor, or steroid which targets an undesired population of cells, such as those of a tumor. Whole protein carriers as well as their antigen-recognizing fragments and their chemically or genetically manipulated counterparts are useful for the targeting portion of the conjugates. This invention includes compounds required for the synthesis of these conjugates, appropriate pharmaceutical compositions of the carrier-drug conjugates, and their method of use.