348111-64-8

Upstream product

• 79-37-8 oxalyl dichloride 
• 85607-00-7 1-(4'-chlorobenzyl)-indole 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 120-72-9 indole 

Downstream Products

• 1000206-52-9 4β-((1-(4-chlorobenzyl)-indol-3-yl)-glyoxylamide)-4-desoxypodophyllotoxin 
• 1061717-04-1 4α-((1-(4-chlorobenzyl)-indol-3-yl)-glyoxyl)-podophyllotoxin 
• 501921-80-8 C₂₁H₁₅Cl₂N₃O₂S 
• 501921-81-9 C₂₀H₁₄ClN₃O₃ 
• 1025355-71-8 C₂₃H₁₉ClN₃O₂⁽¹⁺⁾*I^(1-) 
• 501921-79-5 C₂₄H₁₆ClN₃O₃ 
• 501921-75-1 C₂₀H₁₅ClN₄O₂S₂ 
• 501921-60-4 C₂₃H₁₇ClN₄O₃ 
• 808580-45-2 C₂₆H₁₈ClN₃O₂ 
• 501921-68-2 C₂₄H₂₂ClN₃O₂S 
• 501921-71-7 C₂₁H₁₆ClN₃O₂S 
• 501921-66-0 C₂₁H₁₆ClN₃O₃ 
• 501921-56-8 C₂₁H₁₆ClN₃O₂S 
• 501921-74-0 C₂₁H₁₆ClN₃O₃ 

Relevant academic research and scientific papers

Design and synthesis of bis(indolyl)ketohydrazide-hydrazones: Identification of potent and selective novel tubulin inhibitors

A novel series of ketohydrazide-hydrazones as analogues of naturally occurring coscinamides has been synthesized and evaluated for their anticancer activity against five cancer cell lines. Of the twenty-synthesized ketohydrazide-hydrazones, compounds, 21c, 21f, 21g, 21k and 21o showed cytotoxic effects (less than 50% cell survival) against multiple cancer cell lines when tested at a final concentration of 10?μM. IC50 of three compounds 21f, 21k and 21o was determined to be less than 5?μM for all tested cancer cell lines. Compound 21k exhibited significant anticancer activity against MCF-7, MDA-MB-231, HCT-116 and JURKAT cancer cell lines with IC50 values of 0.8?μM, 0.50?μM, 0.15?μM, and 0.22?μM, respectively. Also, 21k was found to be more selectively cytotoxic against tumor cells when compared to normal cells. Preliminary mechanism of action studies indicated that the most active compound 21k induced caspase-dependent apoptosis in cells. 21k arrests cell cycle in G2/M phase by inhibiting of tubulin polymerization (IC50?=?0.6?μM).

Sequential one-pot synthesis of bis(indolyl)glyoxylamides: Evaluation of antibacterial and anticancer activities

A series of bis(indolyl)glyoxylamides 10a-n has been designed and synthesized. In situ generated indole-3-glyoxalylchloride from the reaction of readily available indole 9 with oxalyl chloride was treated with tryptamine to produce bis(indolyl)glyoxylamides 10a-n in 82-93% yields. All the synthesized bis(indolyl)glyoxylamides were well characterized and tested for their antibacterial activity against Gram-positive and Gram-negative bacterial strains. Compounds 10d, 10g and 10i were found to display potent antibacterial activity against Gram-negative strain. Further, the cytotoxicity of bis(indolyl)glyoxylamides 10a-n were evaluated against a panel of human cancer cell lines. Of the screened analogues, compound 10f (IC50 = 22.34 μM; HeLa, 24.05 μM; PC-3, 21.13 μM; MDA-MB-231 and 29.94 μM; BxPC-3) was identified as the most potent analogue of the series. Exposure of PC-3 cells to either 10a or 10f resulted in increased levels of cleaved PARP1, indicating that bis(indolyl)glyoxylamides induce apoptosis in PC-3 cells. Most importantly, compounds 10d, 10g and 10i were completely ineffective in mammalian cells, suggesting that they target bacterial-specific targets and thus will not display any toxicity in host cells.

Indole- and indolizine-glyoxylamides displaying cytotoxicity against multidrug resistant cancer cell lines

We report herein the SAR studies of a series of indole- and indolizine-glyoxylamides that demonstrate substantial in vitro anti-proliferative activities against cancer cell lines, including multidrug resistance (MDR) phenotypes. The in vitro cytotoxic effects have been demonstrated across a wide array of tumor types of various origins (e.g., breast, colon, uterine).

Design, synthesis and cytotoxicity of novel podophyllotoxin derivatives

A series of novel podophyllotoxin derivatives were designed using association strategy and synthesized by coupling either podophyllotoxin (1) or 4β-amino podophyllotoxin (3) with substituted indol-3-yl-glyoxyl chlorides. Their structures were identified using spectroscopic techniques. These novel derivatives have been evaluated for cytotoxicity in vitro against four human cancer cell lines with comparison to the parent compounds 1, 3 and indibulin (2). Some of the compounds (7a, 7c) showed comparable cytotoxicity to that of podophyllotoxin.

Indole derivatives with apoptosis inducing activity

N-heterocyclyl-2-indolyl-2-oxo-acetamide derivatives (I), their tautomers, stereoisomers (including diastereomers and enantiomers) and their physiologically tolerable salts are new. N-heterocyclyl-2-indolyl-2-oxo-acetamide derivatives (I), their tautomers, stereoisomers (including diastereomers and enantiomers) and their physiologically tolerable salts are new. [Image] R : optionally substituted 6- or 7-quinolyl, excepting 2-methyl-6-quinolyl, optionally substituted 2-, 3-, 6-, 7- or 8-pyridopyrazinyl, or optionally substituted 3-, 4-, 5-, 6- or 7-indazolyl; R 1optionally substituted alkylaryl; R 2H; R 3-R 6H, optionally substituted 1-6C alkyl or 3-7C cycloalkyl, amino (optionally substituted by 1 or 2 1-4C alkyl), halo, 1-4C alkyl substituted by one or more fluoro (preferably trifluoromethyl), cyano, 1-6C cyanoalkyl, 1-6C alkylcarbonyl, carboxy, 1-4C alkoxycarbonyl, carboxy(1-6C)alkyl, 1-6C alkoxycarbonyl(1-6C)alkyl, 1-6C alkoxy, aryl(1-4C)alkoxy (preferably benzyloxy), 1-6C alkoxycarbonylamino, or 1-6C alkoxycarbonylamino(1-6C)alkyl; and X, Y 1O or S. ACTIVITY : Cytostatic. In a human xenograft model of MEXF 462/18N3 melanoma (no more details), administration of 16 mg/kg 2-[1-(4-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-quinolin-6-yl-acetamide on days 1,4,8,11,14,18 and 21 resulted (on day 21) in a tumor volume essentially zero; compare an over 6-fold increase in tumor size for untreated controls. MECHANISM OF ACTION : Tubulin polymerisation inhibitor; Topoisomerase II inhibitor. (I) inhibit both polymerization of tubulin and activity of topoisomerase II, leading to arrest of tumorigenic cells in the G2M phase and thus induction of apoptosis. The compound 2-[1-(4-chlorobenzyl)-1H-indol-3-yl]-2-thioxo-N-quinolin-6-yl-acetamide has EC50 for inhibition of tubulin polymerization ( Cancer Res., 55 (1995) 2325) of 0.97 mu g/ml and at 100 mu M caused over 80% inhibition of topoisomerase II in the assay of Anti Cancer Drug Design, 15 (2000) 413.

2-(1h-indol-3-yl)-2-oxo-acetamides with antitumor activity

2-(1H-Indol-3-yl)-2-oxo-acetamides having antitumor activity, in particular against solid tumors, more precisely colon and lung tumors, of the following formula I: wherein Y is an oxygen of sulfur atom and X, R1, R2, R3, R4 and R5 are as defined in claim 1.

Synthesis and characterization of the biologically active 2-[1-(4-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-pyridin-4-yl acetamide

The spectroscopic characterization of the new potent tubulin inhibitor 2-[1-(4-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-pyridin-4-yl acetamide (D-24851) (7), which is under preclinical development, is described. The synthesis was optimized and follows a straightforward route from the unsubstituted indole via the 1-(4-chlorobenzyl)-indole (3) and the indol-3-yl-2-oxo-acetyl chloride (5) to the indol-3-yl-2-oxo acetamide product. The structure was assigned by sophisticated NMR experiments, for example a 1,1-ADEQUATE experiment, and X-ray crystallography.