16390-26-4

Basic information

• Product Name: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-2-methyl-
• CAS NO: 16390-26-4
• Molecular Formula: C18H14ClNO3
• Molecular Weight: 327.767
• Mol File: 16390-26-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-2-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-2-methyl-(16390-26-4)
• EPA Substance Registry System: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-2-methyl-(16390-26-4)

Safety Data

• Hazardous Substances Data: 16390-26-4(Hazardous Substances Data)

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

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

Relevant articles and documents

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).

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.

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