6532-16-7

Basic information

• Product Name: 1-(Morpholinomethyl)-1H-indole-2,3-dione
• Synonyms: 1-(Morpholinomethyl)-1H-indole-2,3-dione;1-(Morpholinomethyl)isatin
• CAS NO: 6532-16-7
• Molecular Formula: C₁₃H₁₄N₂O₃
• Molecular Weight: 246.2619
• Mol File: 6532-16-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 407.1°Cat760mmHg
• Flash Point: 200°C
• Appearance: /
• Density: 1.332g/cm³
• Vapor Pressure: 7.77E-07mmHg at 25°C
• Refractive Index: 1.608
• CAS DataBase Reference: 1-(Morpholinomethyl)-1H-indole-2,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(Morpholinomethyl)-1H-indole-2,3-dione(6532-16-7)
• EPA Substance Registry System: 1-(Morpholinomethyl)-1H-indole-2,3-dione(6532-16-7)

Safety Data

• Hazardous Substances Data: 6532-16-7(Hazardous Substances Data)

Usage

Synonyms

MLS000715957, AC1OCNJ1, AKOS006160062, SCHEMBL1881859

Structural components

Morpholine group and indole-2,3-dione group

Importance in organic chemistry

Both morpholine and indole-2,3-dione groups are significant in organic chemistry

Importance in pharmaceutical research

Morpholine group is a common structural component in many pharmaceutical drugs

Indole-2,3-dione group

Heterocyclic compound with potential biological activity

Research focus

Pharmacological properties and potential medical applications of the compound

InChI:InChI=1/C13H14N2O3/c16-12-10-3-1-2-4-11(10)15(13(12)17)9-14-5-7-18-8-6-14/h1-4H,5-9H2

Upstream product

• 110-91-8 morpholine 
• 50-00-0 formaldehyd 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 119001-05-7 1-Morpholinomethyl-3-hydroxy-3-(2,2-dimethyl-4-tetrahydropyranonyl)oxindole 

Relevant articles and documents

Structure, anticorrosion and antibacterial evaluation of 1-(Morpholinomethyl)indoline-2,3-dione

In this paper, 3-(4-hydroxyphenylimino)indolin-2-one, was synthesized and analyzed by NMR, MS and X-ray single crystal analysis. The inhibition and the mechanism of the compound on the corrosion of high protective Q235A steel in HCl solution were screened and discussed. The results indicated that it can inhibit the corrosion with moderate inhibition efficiency in different conditions and the inhibition mechanism of the corrosion inhibiting may be mainly contributed to the adsorption. It was screened for antibacterial activity against oilfield water-borne bacteria and it showed good to moderate activity against sulfate reducing bacteria.

Inhibitory effects of isatin Mannich bases on carbonic anhydrases, acetylcholinesterase, and butyrylcholinesterase

The effects of isatin Mannich bases incorporating (1-[piperidin-1-yl (P1)/morpholin-4-yl (P2)/N-methylpiperazin-1-yl (P3)]methyl)-1H-indole-2,3-dione) moieties against human (h) carbonic anhydrase (CA, EC 4.2.1.1) isoenzymes hCA I and hCA II, acetylcholinesterase (AChE), and butyrylcholinesterase (BChE) enzymes were evaluated. P1–P3 demonstrated impressive inhibition profiles against AChE and BChE and also inhibited both CAs at nanomolar level. These inhibitory effects were more powerful in all cases than the reference compounds used for all these enzymes. This study suggests that isatin Mannich bases P1–P3 are good candidate compounds especially for the development of new cholinesterase inhibitors since they were 2.2–5.9 times better inhibitors than clinically used drug Tacrine.

Hybrid pharmacophore design and synthesis of isatin-benzothiazole analogs for their anti-breast cancer activity

A hybrid pharmacophore approach was used to design and synthesize isatin-benzothiazole analogs to examine their anti-breast cancer activity. The cytotoxicity of these compounds were determined using three different human breast tumor cell lines, MDA-MB231, MDA-MB468, MCF7, and two non-cancer breast epithelial cell lines, 184B5 and MCF10A. Although all compounds examined were quite effective on all the cancer cell lines examined, the compounds 4-bromo-1-diethylaminomethyl-1H-indole-2,3-dione (21) and 4-chloro-1- dimethylaminomethyl-3-(6-methyl-benzothiazol-2-ylimino)-1,3-dihydroindol-2-one (5e) emerged as the most active compounds of this series. Importantly, the cytotoxic effect of 21 was 10-15-fold higher on cancer than non-cancer cells, suggesting that this compound can be very effective for the control of breast cancer with low side effects. Since 21 showed effective cytotoxicity on MCF7 cells and arrested the cells at G2/M at a similar concentration, these two phenomena may be closely correlated. We conclude that the isatin-linked benzothiazole analog can serve as a prototype molecule for further development of a new class of anti-breast cancer agents.