84176-62-5

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 1363, 1948 DOI: 10.1021/ja01184a023

InChI:InChI=1/C11H13NO2/c1-3-4-9-7-10(12-8(2)13)5-6-11(9)14/h3,5-7,14H,1,4H2,2H3,(H,12,13)

Upstream product

• 111-90-0 ethoxyethoxyethanol 
• 6622-73-7 4-acetamidophenyl allyl ether 
• 1568-66-7 1-allyloxy-4-nitrobenzene 
• 100-02-7 4-nitro-phenol 
• 557-40-4 Allyl ether 
• 103-90-2 4-acetaminophenol 
• 106-95-6 allyl bromide 
• 408507-62-0 2-Allyl-4-nitroso-phenol 
• 1688-69-3 p-allyloxyaniline 
• 121-69-7 N,N-dimethyl-aniline 
• 35736-25-5 3-(2-hydroxy-5-aminophenyl)-1-propene 
• 108-24-7 acetic anhydride 

Downstream Products

• 857568-37-7 acetic acid-(3-allyl-5-diethylaminomethyl-4-hydroxy-anilide) 
• 861343-05-7 (4-acetylamino-2-allyl-phenoxy)-acetic acid 
• 119118-13-7 N-[2-(4-Chloro-phenylsulfanylmethyl)-2,3-dihydro-benzofuran-5-yl]-acetamide 
• 152974-06-6 3-allyl-4-(3-bromopropyloxy)-acetanilide 
• 58546-89-7 1-benzofuran-5-amine 
• 1394965-64-0 C₂₆H₃₇NO₂ 
• 861295-67-2 N-(3,5-diallyl-4-hydroxy-phenyl)-acetamide 

Relevant academic research and scientific papers

CHEMICAL COMPOUNDS

The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to FormμLa (I): wherein R, R1,P, X, Y, and Z are as defined herein; or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be usefμL in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Synthesis of Phenylpropanoids via Matsuda-Heck Coupling of Arene Diazonium Salts

The Pd-catalyzed Heck-type coupling (Matsuda-Heck reaction) of electron rich arene diazonium salts with electron deficient olefins has been exploited for the synthesis of phenylpropanoid natural products. Examples described herein are the naturally occurring benzofurans methyl wutaifuranate, wutaifuranol, wutaifuranal, their 7-methoxy derivatives, and the O-prenylated natural products boropinols A and C.

Synthesis and SAR studies of 3-allyl-4-prenyloxyaniline amides as potent 15-lipoxygenase inhibitors

15-Lipoxygenases are one of the nonheme iron-containing proteins with ability of unsaturated lipid peroxidation in animals and plants. The critical role of the enzymes in formation of inflammations, sensitivities and some of cancers has been demonstrated in mammalians. Importance of the 15-lipoxygenases leads to development of mechanistic studies, products analysis and synthesis of their inhibitors. In this work new series of the 3-allyl-4-allyoxyaniline amides and 3-allyl-4-prenyloxyaniline amides were designed, synthesized and their inhibitory potency against soybean 15-lipoxygenase were determined. Among the synthetic amides, 3-allyl-4-(farnesyloxy)-adamantanilide showed the most potent inhibitory activity by IC50 value of 0.69 μM. SAR studies showed that in spite of prenyl length increases, the effects of the amide size and its electronic properties on the inhibitory potency became predominant. The SAR studies was also showed that the orientation of allyl and prenyloxy moieties toward Fe core of the SLO active site pocket is the most suitable location for enzyme inhibition.

Therapeutic amines

Compounds of formula I, and their pharmaceutically acceptable salts, STR1 in which R1 and R2 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, phenylalkyl or alkenyl; or NR1 R2 is a heterocyclic group; A is trimethylene optionally substituted by alkyl and the phenyl ring is optionally substituted by substituents such as halogeno, alkenyl, amino, cyano, ureido, alkyl, carbamoylalkyl, alkanoylamino, alkoxycarbonyl, N-alkyl-alkanoylamino, alkanoyl and amines thereof; are inhibitors of squalene synthese and hence useful in treating diseases in which a lowering of cholesterol is desirable. As well as the use of these compounds in medicine, novel compounds, processes for their preparation and pharmaceutical compositions are also referred to.