197073-43-1

Basic information

• Product Name: BOC-4-AMINOCINNAMIC ACID
• Synonyms: BOC-4-AMINOCINNAMIC ACID
• CAS NO: 197073-43-1
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.29
• Mol File: 197073-43-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BOC-4-AMINOCINNAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-4-AMINOCINNAMIC ACID(197073-43-1)
• EPA Substance Registry System: BOC-4-AMINOCINNAMIC ACID(197073-43-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 197073-43-1(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 17570-30-8 trans-p-aminocinnamic acid 
• 79-10-7 acrylic acid 
• 6163-58-2 tris-(o-tolyl)phosphine 
• 131818-17-2 tert-butyl (4-bromophenyl)carbamate 
• 1538-75-6 2,2-dimethylpropanoic anhydride 

Downstream Products

• 1041867-85-9 tert-butyl N-{4-[(E)-3-(1H-1,2,3-benzotriazole-1-yl)-3-oxo-1-propenyl]phenyl}carbamate 
• 1392506-35-2 tert-butyl (4-((E)-3-(((R)-1-(((R)-1-((7-chloroquinolin-4-yl)amino)-1-oxo-4-phenylbutan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-3-oxoprop-1-en-1-yl)phenyl)carbamate 

Relevant articles and documents

Construction of supramolecular polymers with alternating α-, β-cyclodextrin units using conformational change induced by competitive guests

Supramolecular polymers having alternating α- and β-cyclodextrin (CD) units have been prepared by using conformational change induced by competitive guests. Although each CD unit does not form intermolecular complexes, a mixture of an α-CD derivative and a β-CD derivative formed intermolecular complexes to give supramolecular polymers having alternating CD units. This is the first example of construction of supramolecular polymers with alternating α-, β-cyclodextrin units. Copyright

Chiral supramolecular polymers formed by host-guest interactions

α-Cyclodextrin with a p-t-butoxyaminocinnamoylamino group in the 3-position (3-p-tBocCiNH-α-CD) has been found to form a supramolecular polymer in an aqueous solution. The degree of polymerization of the supramolecular polymer is higher than 15

Structural Fine-Tuning of Desmuramylpeptide NOD2 Agonists Defines Their in Vivo Adjuvant Activity

We report on the design, synthesis, and biological evaluation of a series of nucleotide-binding oligomerization-domain-containing protein 2 (NOD2) desmuramylpeptide agonists with improved in vitro and in vivo adjuvant properties. We identified two promising compounds: 68, a potent nanomolar in vitro NOD2 agonist, and the more lipophilic 75, which shows superior adjuvant activity in vivo. Both compounds had immunostimulatory effects on peripheral blood mononuclear cells at the protein and transcriptional levels, and augmented dendritic-cell-mediated activation of T cells, while 75 additionally enhanced the cytotoxic activity of peripheral blood mononuclear cells against malignant cells. The C18 lipophilic tail of 75 is identified as a pivotal structural element that confers in vivo adjuvant activity in conjunction with a liposomal delivery system. Accordingly, liposome-encapsulated 75 showed promising adjuvant activity in mice, surpassing that of muramyl dipeptide, while achieving a more balanced Th1/Th2 immune response, thus highlighting its potential as a vaccine adjuvant.

Efficient synthesis of 1,4-thiazepanones and 1,4-thiazepanes as 3d fragments for screening libraries

1,4-Thiazepanes and 1,4-thiazepanones represent seven-membered ring systems with highly 3D character and are currently underrepresented in fragment screening libraries. A nuclear magnetic resonance (NMR) fragment screen identified 1,4-acylthiazepanes as new BET (bromodomain and extraterminal domain) bromodomain ligands; however, an efficient and readily diversified synthesis for library development has not been reported. Here we report a one-pot synthesis using α,β-unsaturated esters and 1,2-amino thiols to form 1,4-thiazepanones as precursors to 1,4-thiazepanes with high 3D character. This reaction proceeds in reasonable time (0.5-3 h) and in good yield and tolerates a broad scope of α,β-unsaturated esters. Several 1,4-thiazepanes were synthesized by a two-step transformation and were characterized as new BET bromodomain ligands using protein-observed 19F NMR. This synthesis should provide ready access to diverse 3D fragments for screening libraries.

Preparation and synthetic applications of N-(α,β-unsaturated acyl)-α-amino acid derivatives

N-(α,β-Unsaturated acyl)-α-amino acids, amides and esters are structural motifs of many biologically active natural products. An alternate and advantageous approach for the synthesis of N-(α,β-unsaturated acyl)-α-amino acid derivatives is developed via ac

Cinnamoyl inhibitors of tissue transglutaminase

(Figure Presented) Transglutaminases (TGases) catalyze the intermolecular cross-linking of certain proteins and tissue TGases (TG2) are involved in diverse biological processes. Unregulated, high TGase activities have been implicated in several physiological disorders, but few reversible inhibitors of TG2 have been reported. Herein, we report the synthesis of a series of novel trans-cinammoyl derivatives, discovered to be potent inhibitors of guinea pig liver transglutaminase. The most effective inhibitors evaluated can be sorted into two subclasses: substituted cinnamoyl benzotriazolyl amides and the 3-(substituted cinnamoyl)pyridines, referred to more commonly as azachalcones. Kinetic evaluation of both of these subclasses revealed that they display reversible inhibition and are competitive with acyl donor TGase substrates at IC50 values as low as 18 μM. An analysis of structure - activity relationships within these series of inhibitors permitted the identification of potentially important binding interactions. Further testing of some of the most potent inhibitors demonstrated their selectivity for TG2 and their potential for further development.

Cyclic imino derivatives and pharmaceutical compositions containing them

The invention relates to cyclic imino compounds which have, inter alia, valuable pharmacological properties, especially inhibitory effects on cell aggregation, pharmaceutical compositions which contain these compounds and processes for preparing them.

PYRROLYLPHENYL-SUBSTITUTED HYDROXAMIC ACID DERIVATIVES

Disclosed are the pyrrolylphenyl-substituted hydroxamic acid derivatives of the formula wherein R represents hydrogen, lower alkyl, halogen or lower alkoxy; R1 and R2 independently represent hydrogen, lower alkyl or aryl; Y represents a direct bond, lower alkylene, lower alkenylene, lower alkadienylene, (thio, sulfinyl or sulfonyl)-lower alkylene or oxy-lower alkylene; Z represents wherein R3 represents hydrogen or acyl; R4 represents lower alkyl, C3-C7-cycloalkyl, aryl or aryl-lower alkyl; or Z represents wherein R3 represents hydrogen or acyl; R5 represents lower alkyl, C3-C7-cycloalkyl, aryl, aryl-lower alkyl, amino or N-(mono-or di-lower alkyl)-amino; R6 and R7 represent hydrogen or lower alkyl; and pharmaceutically acceptable salts thereof provided that R3 represents hydrogen; which are useful as selective lipoxygenase inhibitors, methods for preparation thereof, pharmaceutical compositions comprising said compounds, and a method of inhibiting lipoxygenase and of treating diseases in mammals which are responsive to lipoxygenase inhibition using said compounds and pharmaceutical compositions comprising said compounds of the invention.