16390-26-4

Usage

Derived from

Plant hormone indole-3-acetic acid (IAA)

Type

Synthetic auxin

Common Uses

Growth regulator for plants in agriculture, stimulating root development, fruit set, and flowering

Structural Modification

Addition of a 4-chlorobenzoyl group to the 1 position and a methyl group to the 2 position of the indole ring

Enhanced Activity

The structural modification enhances the compound's auxin activity

Potential Applications

Promoting plant growth and increasing crop yield in horticulture and agriculture.

Upstream product

• 123-76-2 levulinic acid 
• 55130-75-1 N₁-(4-chlorobenzoyl)-N₁-phenylhydrazine hydrochloride 
• 220465-91-8 1-(2-aminophenyl)prop-1-yne 
• 615-43-0 2-iodophenylamine 
• 95-20-5 2-methyl-1H-indole 
• 502607-41-2 benzyl 2-(2-methyl-1H-indol-3-yl)acetate 
• 53472-24-5 benzyl 2-(1-(4-chlorobenzoyl)-2-methyl-1H-indol-3-yl)acetate 
• 122-01-0 4-chloro-benzoyl chloride 
• 1912-43-2 2-methyl-3-indoleacetic acid 
• 345960-80-7 acetaldehyde N₁-(4-chlorobenzoyl)-N₁-phenylhydrazone 
• 935-07-9 acetaldehyde phenylhydrazone 
• 100-63-0 phenylhydrazine 

Relevant academic research and scientific papers

Well-Defined Noble Metal Single Sites in Zeolites as an Alternative to Catalysis by Insoluble Metal Salts

Insoluble precious metal chlorides in polymeric form (i.e., PtCl2, PdCl2, AuCl, RhCl3) are commonly used as catalysts for a plethora of organic reactions in solution. Here we show that only the minor soluble fraction of these precious metal chlorides (typically 5-30%) is catalytically active for the hydroamination, hydroalkoxylation, hydrosilylation, and cycloisomerization of alkynes and alkenes, and that the resting insoluble metal is catalytically useless. To circumvent this waste of precious metal and follow a rational design, we generate here well-dispersed Pt(II) and Pd(II) single sites on zeolite Y, with an exquisite control of the Lewis acidity, to catalyze different hydroaddition reactions to alkynes and alkenes with up to 104 catalytic cycles (at least 2 orders of magnitude superior to precious metal chlorides) and with high isolated yields (82-99%, >15 examples).

Design and synthesis of indomethacin analogues that inhibit P-glycoprotein and/or multidrug resistant protein without Cox inhibitory activity

We designed and synthesized conformationally restricted analogues and regioisomers of the nonsteroidal anti-inflammatory drug indomethacin. Evaluation of the inhibitory effects of these compounds on COX, P-glycoprotein, and multidrug resistance indicated that NSAIDS modulation of multidrug-resistant P-glycoprotein and multidrug-resistant protein-1 is not associated with COX-1 and COX-2 inhibitory activities.

Indomethacin analogues that enhance doxorubicin cytotoxicity in multidrug resistant cells without cox inhibitory activity

Conformationally restricted indomethacin analogues were designed and prepared from the corresponding 2-substituted indoles, which were synthesized by a one-pot isomerization/enamide-ene metathesis as the key reaction. Conformational analysis by calculations, NMR studies, and X-ray crystallography suggested that these analogues were conformationally restricted in the s-cis or the s-trans form due to the 2-substituent as expected. Their biological activities on cyclooxygenase-1 (COX-1) inhibition, cyclooxygenase-2 (COX-2) inhibition, and modulation of MRP-1-mediated multidrug resistance (MDR) are described. Some of these indomethacin analogues enhanced doxorubicin cytotoxicity, although they do not have any COX inhibitory activity, which suggests that the MDR-modulating effect of an NSAID can be unassociated with its COX-inhibitory activity. This may be an entry into the combination chemotherapy of doxorubicin with a MDR modulator.

2-ARYL-ACETIC ACIDS, THEIR DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Selected 2-arylacetic acids, their derivatives and pharmaceutical compositions that contain these compounds are useful in inhibiting chemotactic activation of neutrophils (PMN leukocytes) induced by the interaction of Interleukin-8 (IL-8) with CXCR1 and CXCR2 membrane receptors. The compounds are used for the prevention and treatment of pathologies deriving from said activation. In particular, 2(ortho)-substituted arylacetic acids or their derivatives, such as amides and sulfonamides, lack cyclo-oxygenase inhibition activity and are particularly useful in the treatment of neutrophil-dependent pathologies such as psoriasis, ulcerative colitis, melanoma, chronic obstructive pulmonary disease (COPD), bullous pemphigoid, rheumatoid arthritis, idiopathic fibrosis, glomerulonephritis and in the prevention and treatment of damages caused by ischemia and reperfusion.

Synthesis of indomethacin analogues for evaluation as modulators of MRP activity

Synthesis of a range of indomethacin analogues, required for investigation in combination toxicity assays, bearing both N-benzyl and N-benzoyl groups, is described. Copyright