143262-19-5

Usage

Synthetic ester derivative

1H-indole-1-carboxylic acid The compound is synthesized from 1H-indole-1-carboxylic acid, a naturally occurring organic compound, by modifying its structure to create a derivative with different properties.

Pharmaceutical industry use

Building block for synthesis of medicinal compounds This chemical is commonly used as an intermediate in the synthesis of various pharmaceutical compounds, serving as a building block for creating a range of medicinal molecules.

Therapeutic applications

Anti-inflammatory and analgesic agent The compound has potential therapeutic applications, including serving as an anti-inflammatory to reduce swelling and as an analgesic to relieve pain.

Structure and properties

Valuable component in drug development The unique structure and properties of this chemical make it a valuable component in the development of new drugs and pharmaceutical formulations, contributing to the creation of innovative treatments and therapies.

Upstream product

• 143262-10-6 1-(tert-butoxycarbonyl)indoline 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 496-15-1 1-indoline 
• 24424-99-5 di-tert-butyl dicarbonate 

Relevant academic research and scientific papers

CANCER TREATMENTS TARGETING CANCER STEM CELLS

Disclosed are compounds, methods, compositions, and kits that allow for treating cancer by, e.g., targeting cancer stem cells. In some embodiments, the cancer is colorectal cancer, gastric cancer, gastrointestinal stromal tumor, ovarian cancer, lung cancer, breast cancer, pancreatic cancer, prostate cancer, testicular cancer, or lymphoma. In some embodiments, the cancer is liver cancer, endometrial cancer, leukemia, or multiple myeloma. The compounds utilized in the disclosure are of Formula (0), (O'), and (I):

Asymmetric Deprotonations: Lithiation of N-(tert-Butoxycarbonyl)indoline with sec-Butyllithium/ (-)-Sparteine

The asymmetric lithiation of N-Boc indoline (1) with s-BuLi/(-)-sparteine and subsequent substitution provides the 2-substituted N-Boc indolines 3 and 5-11 with excellent enantiomeric ratios and in variable yields. The asymmetric lithiation-substitution sequence with N-Boc-7-chloroindoline (12) provides products 13-19 with good enantiomeric ratios. Mechanistic investigation establishes that the enantioselectivities arise from an initial asymmetric deprotonation to provide the enantioenriched and configurationally stable organolithium intermediates (S)-28 and (S)-29, which react stereoselectively with electrophiles.

α-Lithioamine Synthetic Equivalents: Synthesis of Diastereoisomers from Boc Derivatives of Cyclic Amines

Sequences of α'-lithiations and electrophilic substitutions of Boc-pyrrolidines, Boc-piperidines, and Boc-hexahydroazepines that provide compounds which are substituted adjacent to nitrigen are reported, and the pathways of the reactions are discussed.By this methodology monosubstituted 2 and disubstituted 2,4, 2,6, and 2,5 Boc-piperidines are obtained as single or separable diastereoisomers consistent with equatorial lithiations and retentive electrophilic substitution in chair conformations.Both cis and trans 2,6-disubstituted diastereoisomers can be prepared, and control of diastereoselectivity is demonstrated by syntheses of solenopsin A, a 2,6-trans-disubstituted piperidine, and of Boc-dihydropinidine, a 2,6-cis-disubstituted piperidine.In the case of 3-methoxy-Boc-piperidine elimination of methoxide occurs upon lithiation, and with cis-2,4-disubstituted Boc-piperidines the electrophile is introduced with trans stereochemistry at C-6.These reactions are suggested to involve twist boat conformations consistent with an X-ray crystal structure of 2-methyl-6-(trimethylstannyl)-4-phenyl-N-Boc-piperidine.Boc-pyrrolidine lithiates more rapidly than Boc-piperidine, provides 2-substituted products with electrophiles, and on further lithiation-substitution gives 2,5-cis- and -trans substituted products.Boc-perhydroazepine provides 2-substituted products by the sequence and on further lithiation-substitution gives 2,7-trans-disubstituted products.

DIRECTED LITHIATION OF 1-(tert-BUTOXYCARBONYL)INDOLINES. A CONVENIENT ROUTE TO 7-SUBSTITUTED INDOLINES

1-(tert-Butoxycarbonyl)indolines were regioselectively lithiated at 7-position with s-BuLi-TMEDA in ether or THF at -78 deg C.The lithiated species were reacted with a range of electrophiles to give 7-substituted indoline derivatives.