62718-62-1

Upstream product

• 1216-21-3 ethyl (E)-3-(4-butylphenyl)acrylate 
• 79887-09-5 (4-butylphenyl)acetylene 
• 916576-33-5 trans-4-n-butylcinnamic acid n-butyl ester 
• 104-51-8 1-butylbenzene 
• 1200-14-2 4-(n-butyl)benzaldehyde 
• 141-82-2 malonic acid 

Downstream Products

• 110683-52-8 (E)-3-(4-Butyl-phenyl)-N-[4-oxo-2-(1H-tetrazol-5-yl)-4H-chromen-8-yl]-acrylamide 
• 110683-43-7 (E)-3-(4-Butyl-phenyl)-N-[3-(1H-tetrazol-5-yl)-2,3-dihydro-benzo[1,4]dioxin-5-yl]-acrylamide 
• 1038997-12-4 3-[(E)-3-(4-n-butylphenyl)-2-propenoyl]-2-thiazolidinethione 
• 1209-17-2 3-(4-Butyl-phenyl)-propionamid 
• 1209-19-4 3-(4'-butylphenyl)propanoic acid 
• 1209-18-3 4-Butyl-trans-cinnamamid 

Relevant academic research and scientific papers

Semireduction of alkynoic acids via a transition metal-free α borylation-protodeborylation sequence

A method for the semi-reduction of alkynoic acids through an α-borylation and subsequent protodeborylation mechanism has been developed. The transition metal-free protocol is achieved through the activation of bis(pinacolato)diboron by an in situ generated carboxylate moiety yielding aryl acrylic acids. Our studies demonstrate an unprecedented dual role for the carboxylate anion that involves the activation of the diboron reagent and a directing effect in the α-borylation.

PHENYLALKYLCARBOXYLIC ACID DELIVERY AGENTS

The present invention provides phenylalkylcarboxylic acid compounds and compositions containing such compounds which facilitate the delivery of biologically active agents.

Mass spectrometric screening of enantioselective Diels-Alder reactions

(Chemical Equation Presented) A rapid cat. scan: Mass spectrometric monitoring of reaction intermediates of the retro-Diels-Alder reaction has allowed the rapid screening of catalysts for enantioselective Diels-Alder reactions (see scheme). Copper catalysts as well as metal-free organocatalysts were tested. A protocol for the simultaneous screening of catalyst mixtures has also been developed, which offers new possibilities for high-throughput catalyst development.

Discovery of potent, orally available vanilloid receptor-1 antagonists. Structure-activity relationship of N-aryl cinnamides

The vanilloid receptor-1 (TRPV1 or VR1) is a member of the transient receptor potential (TRP) family of ion channels and plays a role in regulating the function of sensory nerves. A growing body of evidence demonstrates the therapeutic potential of TRPV1 modulators, particularly in the management of pain. As a result of our screening efforts, we identified (E)-3-(4-tert- butylphenyl)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylamide (1), an antagonist that blocks the capsaicin-induced and pH-induced uptake of 45Ca2+ in TRPV1-expressing Chinese hamster ovary cells with IC50 values of 17 ± 5 and 150 ± 80 nM, respectively. In this report, we describe the synthesis and structure-activity relationship of a series of N-aryl cinnamides, the most potent of which (49a and 49b) exhibit good oral bioavailability in rats (Foral = 39% and 17%, respectively).

New potent antagonists of leukotrienes C4 and D4. 1. Synthesis and structure-activity relationships

(p-Amylcinnamoyl)anthranilic acid (3a) had moderate antagonist activities against LTD4-induced smooth muscle contraction on guinea pig ileum and LTC4-induced bronchoconstriction in anesthetized guinea pigs. Modifications were made in the hydrophobic part (cinnamoyl moiety) and the hydrophilic part (anthranilate moiety) of 3a. A series of 8-(benzoylamino)-2-tetrazol-5-yl-1,4-benzodioxans and 8-(benzoylamino)-2-tetrazol-5-yl-4-oxo-4H-1-benzopyrans were revealed to be potent antagonists of leukotrienes C4 and D4. Among both series, ONO-RS-347 (18k) and ONO-RS411 (19h) were the most potent and orally active antagonists, respectively. Structure-activity relationships are discussed.