70806-55-2

Usage

Uses

trans-Tranilast is used to treat bronchial asthma, allergic rhinitis and atopic dermatitis.

Upstream product

• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 134-20-3 2-carbomethoxyaniline 
• 53947-84-5 2-[(2-carboxyacetyl)amino]benzoic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 118-92-3 anthranilic acid 
• 140-10-3 (E)-3-phenylacrylic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 99-05-8 meta-aminobenzoic acid 
• 91920-58-0 N-(cis-3,4-dimethoxycinnamoyl)anthranilic acid 

Downstream Products

• 99664-42-3 C₃₆H₃₄N₂O₁₀ 
• 93755-79-4 C₃₆H₃₄N₂O₁₀ 
• 91920-58-0 N-(cis-3,4-dimethoxycinnamoyl)anthranilic acid 
• 53902-28-6 2-[[3-(3,4-dimethoxyphenyl)-1-oxopropyl]amino]benzoic acid 
• 93755-78-3 2-(3,4-dimethoxy-trans-styryl)-benzo[d][1,3]oxazin-4-one 

Relevant academic research and scientific papers

N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites

The transient receptor potential ankyrin 1 (TRPA1) channel is a non-selective cation channel, which detects noxious stimuli leading to pain, itch and cough. However, the mechanism(s) of channel modulation by many of the known, non-reactive modulators has not been fully elucidated. N-Cinnamoylanthranilic acid derivatives (CADs) contain structural elements from the TRPA1 modulators cinnamaldehyde and flufenamic acid, so it was hypothesized that specific modulators could be found amongst them and more could be learnt about modulation of TRPA1 with these compounds. A series of CADs was therefore screened for agonism and antagonism in HEK293 cells stably transfected with WT-human (h)TRPA1, or C621A, F909A or F944A mutant hTRPA1. Derivatives with electron-withdrawing and/or electron-donating substituents were found to possess different activities. CADs with inductive electron-withdrawing groups were agonists with desensitising effects, and CADs with electron-donating groups were either partial agonists or antagonists. Site-directed mutagenesis revealed that the CADs do not undergo conjugate addition reaction with TRPA1, and that F944 is a key residue involved in the non-covalent modulation of TRPA1 by CADs, as well as many other structurally distinct non-reactive TRPA1 ligands already reported.

Increased immune cell infiltration in patient-derived tumor explants treated with Traniplatin: An original Pt(iv) pro-drug based on Cisplatin and Tranilast

Elevated intra-tumoral immune infiltrate is associated with an improved prognosis in cancer of distinct origins. Traniplatin (TPT) is a novel platinum(iv) pro-drug based on Cisplatin (CDDP) and the marketed drug Tranilast. When compared in vitro to Cisplatin, TPT showed increased cytotoxic activity against colon and lung cancer cells but decreased activity against immune cells. In addition, TPT efficiency was evaluated in tumor explants derived from colorectal cancer samples from patients subjected to intended curative surgery. TPT induced strong intra-tumoral cytotoxic activity yet was associated with an elevated presence of immune cell infiltrate, suggesting a reduced cytotoxic activity against immune cells in colorectal cancer.

PRODUCTION OF RED BLOOD CELLS AND PLATELETS FROM STEM CELLS

This disclosure provides methods of making a megakaryocyte-erythroid progenitor cell (MEP), comprising differentiating a stem cell into a MEP in culture in the presence of an aryl hydrocarbon receptor (AhR) agonist. In some embodiments the stem cell is a pluripotent stem cell. In some embodiments the MEP co-expresses CD41 and CD235. In some embodiments the number of MEPs produced in the culture increases exponentially. Methods of making a red blood cell (RBC) by culturing a MEP in the presence of an AhR agonist are also provided. Methods of making a megakaryocyte and/or a platelet, comprising culturing a MEP in the presence of an AhR modulator are also provided. In some embodiments the AhR modulator is an AhR antagonist. This disclosure also provides compositions comprising at least 1 million MEPs per ml and compositions in which at least 50% of the cells are MEPs.

FUSED RING ANALOGUES OF ANTI-FIBROTIC AGENTS

The present invention relates to arylcarbonyl and heteroarylcarbonyl anthranilate compounds that may be useful as anti-fibrotic agents. The present invention also relates to methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment disorders.

COMBINATION THERAPY OF ARTHRITIS WITH TRANILAST

Combination therapy is disclosed herein for the treatment an arthritic condition (e.g. rheumatoid arthritis, osteoarthritis or psoriatic arthritis). The therapies disclosed herein comprise administering tranilast or an analogous compound in combination wi

Evaluation and optimization of antifibrotic activity of cinnamoyl anthranilates

Tranilast is an anti-inflammatory drug in use for asthma and atopic dermatitis. In studies over the last decade it has been revealed that tranilast can reduce fibrosis occurring in the kidney during diabetes, thereby delaying and/or preventing kidney dysfunction. We report a structure-activity study aimed at optimizing the antifibrotic activity of tranilast. A series of cinnamoyl anthranilates were prepared and assessed for their ability to prevent TGF-β-stimulated production of collagen in cultured renal mesangial cells. We reveal derivatives with improved potency and reduced cellular toxicity relative to tranilast. 3-Methoxy-4-propargyloxycinnamoyl anthranilate reduces albuminuria in a rat model of progressive diabetes, and thus has potential as an innovative treatment for diabetic nephropathy.

THERAPEUTIC COMPOUNDS

Substituted cinnamoyl anthranilate compounds exhibiting anti-fibrotic activity; or derivatives thereof, analogues thereof, pharmaceutically acceptable salts thereof, and metabolites thereof; with the proviso that the compound is not Tranilast.

A simple two-step synthesis of avenanthramides, constituents of oats (Avena sativa L)

A simple two-step general procedure has been developed to prepare naturally occurring and synthetic avenanthramides, constituents of oats (Avena sativa L). Reaction of anthranilic acid 1 with Meldrum's acid 2 gives half amide of malonic acid 3 which on condensation with different benzaldehyde derivatives 4a-m gives avenanthramides 5a-m of which 5a-d are natural, 5e-g are their methyl ethers and 5h-m are synthetic.

Different Photodimerization Behaviour of Tranilast in α-, β- and γ-Cyclodextrin Complexes: Cavity-size and Stoichiometry Dependence

The effects of α-, β- and γ-cyclodextrins (CDxs) on the photoisomerization and photodimerization of an antiallergic drug tranilast have been kinetically investigated. α- and β-CDxs decelerate both the photoisomerization and photodimerization of 1, showing saturation kinetics, due to 1:1 complex formation.On the other hand, γ-CDx accelerates the photodimerization of 1 at higher 1:γ-CDx molar ratios, but decelerates it at lower 1:γ-CDx molar ratios.The photoisomerization of 1 is decelerated over the γ-CDxconcentration range employed.The continuous variation plot of CDx-induced circular dichroism intensities of 1 and the solubility data indicate that 1 forms inclusion complexes with γ-CDx in different stoichiometry, depending on the guest:host molar ratio.At higher 1:γ-CDx molar ratios, 1 formed the 2:1 (guest:host) complex which accelerates by about 5500 times, the dimerization of 1.With increasing γ-CDx concentration, 1:1 and 1:2 complexes are formed and the dimerization rate of 1 decreases markedly; in particular, the 1:2 complex decelerates it by 19300 times.The results reveal clear evidence for the cavity-size- and stoichiometry-dependent dimerization of 1 in CDx complexes.