153034-33-4

Upstream product

• 26906-01-4 2-allyloxybenzyl alcohol 
• 124-63-0 methanesulfonyl chloride 
• 90-02-8 salicylaldehyde 
• 28752-82-1 2-(allyloxy)benzaldehyde 

Downstream Products

• 149244-04-2 1-allyloxy-2-azidomethylbenzene 
• 918655-65-9 (Z)-1,4-bis(2-(chloromethyl)phenoxy)but-2-ene 
• 918655-67-1 (E)-1,4-bis(o-chloromethylphenoxy)-2-butene 
• 1413932-61-2 1-(allyloxy)-2-({[2-(allyloxy)benzyl]oxy}methyl)benzene 
• 1413932-62-3 1-(allyloxy)-2-({[2-(allyloxy)benzyl]sulfanyl}methyl)benzene 
• 1413932-63-4 2,2'-sulfonylbis(methylene)bis(allyloxybenzene) 

Relevant academic research and scientific papers

The winding road of the uvaretin class of natural products: From total synthesis to bioactive agent discovery

Herein, we disclose the development of a synthetic route to gain access to the uvaretin class of chalcone natural products. In this, the construction of a small library was achieved, and the collection was evaluated for cytotoxicity and other biological properties. Uvaretin (1) was accessed via a seven-step route in an overall yield of 15.1%. Within this route, the unsaturated enone variant of uvaretin (2), also a natural product, was accessed in a 16.7% yield over six steps. This route provides a nearly three-fold increase in yields of 1 and 2 in comparison to the previous synthetic route accessing them in 5.8% and 3.0% overall yields, respectively. Evaluation of 1 and 2 revealed IC50 values between 2.0 and 5.1 μM in the cancerous cell lines HeLa, U937, A549, and MIA PaCa-2. Screening of the whole chalcone library set led to the discovery of over 30 compounds, within six cancerous cell lines, possessing single digit μM IC50 activity as sole agents. Furthermore, multiple library members were found to possess promising potentiating properties with known chemotherapeutic agents.

Ring-closing metathesis reaction-based synthesis of new classes of polyether macrocyclic systems

Ring closing metathesis (RCM) reactions of suitable substrates having terminal olefins, which are assembled from various linkers and hydroxy benzaldehydes and syntheses of a wide range of 16-30 membered, new crown ether-type polyether, aza-polyether, bis aza-polyether macrocycles and dilactone moiety embedded polyether macrocycles (macrolides) are reported. After the ring-closure reaction, installation of different functional groups and functional group modification on the periphery of the synthesized polyether/crown ether macrocycles obtained in the RCM reactions are accomplished using the epoxidation, oxidation and catalytic hydrogenation-based synthetic transformations. Along this line, the syntheses of a variety of polyether macrocycles possessing epoxide or α-hydroxy ketone or 1,2-diol functionalities at the periphery have been shown. Furthermore, the synthesized α-hydroxy ketone functionality installed polyether macrocycles were subjected to the allylation and Reformatsky type reactions to obtain homoallyl alcohol moiety-based and lactone ring-appended polyether macrocycles.

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

The disclosure generally relates to compounds of formula I, including compositions and methods for treating human immunodeficiency virus (HIV) infection. The disclosure provides novel inhibitors of HIV, pharmaceutical compositions containing such compounds, and methods for using these compounds in the treatment of HIV infection. Formule (I)

MACROCYCLIC PURINES FOR THE TREATMENT OF VIRAL INFECTIONS

This invention relates macrocyclic purine derivatives having formula (I), processes for their preparation, pharmaceutical compositions, and their use in treating viral infections.

On the stereochemistry of the olefinic double bond in 13-membered heterocyclic rings accessible by ring-closing metathesis reaction

13-Membered heterocyclic ring analogs of the core structure of manzamine alkaloids were synthesized by ring closing metathesis (RCM) reaction. The influence of a remote heteroatom (N, O, S) on E/Z stereochemistry of the olefinic double bond formed in RCM reaction using Grubbs 1st and 2nd generation ruthenium carbene complexes was evaluated. Studies show that RCM reaction is kinetically controlled and the hetero atoms influence the double bond stereochemistry.

Synthesis of olefinic crown diamides and their conversion into pyrazolino macrocycles: Promising photoluminescent crown compounds

Macrocyclic crown diamides with 16- or 24-membered rings containing E- and Z-olefinic double bonds were synthesized either by bisalkylation or by ring-closing metathesis (RCM) techniques. The two methods were evaluated and compared with regard to yield and to product stereochemistry. Isomerization of some Z-olefinic macrocycles to their corresponding E-isomers was achieved using Grubbs' catalyst second generation. Some of the required starting dials, diols and bishalo compounds were prepared by different routes including cross-metathesis (CM). The latter was compared with other investigated methods. Some of the olefinic macrocycles were subjected to cycloaddition reactions with diphenylnitrileimine to give the corresponding pyrazolino macrocycles. The latter showed interesting emission spectra. Georg Thieme Verlag Stuttgart.

Direct halogenation of alcohols and their derivatives with tert-Butyl halides in the ionic liquid [pmIm]Br under sonication conditions - A novel, efficient and green methodology

A novel halogenating reagent system for direct halogenation of alcohols has been developed. tert-Butyl bromide, chloride and iodide in combination with the ionic liquid [pmIm]Br have been found to convert alcohols into the corresponding bromides, chlorides and iodides under sonication conditions (or heating) in good yields. Although a variety of primary and secondary alcohols participated in this reaction without any difficulty, tertiary alcohols remained inert. Several alcohol derivatives such as OTMS, OTBDMS, OAc, OTS and OTHP are also transformed into the corresponding halides in one-pot fashion by this procedure. A plausible rationale for this transformation is also presented. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Cycloalkano-indole and -azaindole derivatives

Cycloalkano-indole and -azaindole derivatives are prepared by reaction of appropriately substituted carboxylic acids with amines. The cycloalkano-indole and -azaindole derivatives are suitable as active compounds for medicaments, preferably antiatheroscle

Steric acceleration of intramolecular cycloaddition reactions

Use of conformational constraints, induced by different ortho-substituents in 1-allyloxy-2-(substituted)methylbenzenes, where the substituent is a 1,3-dipole such as the azide or 3-oxidopyridinium group, can be employed to accelerate the 1,3-dipolar cycloaddition reaction. In this manner cycloadditions that otherwise do not proceed can be forced to react.