41534-69-4

Upstream product

• 1885-29-6 anthranilic acid nitrile 
• 41534-70-7 (2-cyanophenyl)carbamic acid ethyl ester 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 41534-72-9 ethyl 2-benzoyl-3-(2-bromoacetamido)-1H-indole-1-carboxylate 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel indole-pyrimidine hybrids bearing morpholine and thiomorpholine moieties

Based on our previous screening hit compound 1, a series of novel indole-pyrimidine hybrids possessing morpholine or thiomorpholine moiety were synthesized via an efficient one-pot multistep synthetic method. The antiproliferative activities of the synthesized compounds were evaluated in?vitro against four cancer cell lines including HeLa, MDA-MB-231, MCF-7, and HCT116. The results revealed that most compounds possessed moderate to excellent potency. The IC50 values of the most promising compound 15 are 0.29, 4.04, and 9.48?μM against MCF-7, HeLa, and HCT116?cell lines, respectively, which are 48.0, 4.9, and 1.8 folds more active than the lead compound 1. Moreover, fluorescence-activated cell sorting analysis revealed that compound 14 showing the highest activity against HeLa (IC50?=?2.51?μM) displayed a significant effect on G2/M cell-cycle arrest in a concentration-dependent manner in HeLa cell line. In addition, representative nine active hybrids were evaluated for tubulin polymerization inhibitory activities, and compound 15 exhibited the most potent anti-tubulin activity showing 42% inhibition at 10?μM. These preliminary results encourage a further investigation on indole-pyrimidine hybrids for the development of potent anticancer agents that inhibit tubulin polymerization.

Synthesis, biological evaluation, and molecular docking investigation of 3-amidoindoles as potent tubulin polymerization inhibitors

A series of novel 3-amidoindole derivatives possessing 3,4,5-trimethoxylphenyl groups were synthesized and evaluated for their antiproliferative and tubulin polymerization inhibitory activities. Some of them demonstrated moderate to potent activities in vitro against six cancer cell lines including MCF-7, MDA-MB-231, BT549, T47D, MDA-MB-468, and HS578T. The most active compound 27 inhibited the growth of T47D, BT549, and MDA-MB-231 cell lines with IC50 values at 0.04, 3.17, and 6.43 μM, respectively. Moreover, the flow cytometric analysis clearly revealed that compound 27 significantly inhibited growth of breast cancer cells through arresting cell cycle in G2/M phase via a concentration-dependent manner. In addition, the compound also exhibited the most potent anti-tubulin activity with IC50 values of 9.5 μM, which was remarkable, compared to CA-4. Furthermore, molecular docking analysis demonstrated the interaction of the compound 27 at the colchicine-binding site of tubulin. These preliminary results suggest that compound 27 is a very promising tubulin-binding agent and is worthy of further investigation aiming to the development of new potential anticancer agents.

Synthesis and analgesic activity of some 1-benzofurans, 1-benzothiophenes and indoles

3-Unsubstituted 1-benzofurans 1e and 1f, 3-methyl-1-benzofurans 1a-1d, and 3-amino-1-benzofurans 2a-21, as well as 3-amino-1-benzothiophenes 3a, 3b and 3-aminoindoles 4a-4f, 11a, and 11b were prepared and tested as analgesics. The 3-amino-1-benzofurans 2 were prepared from the corresponding 2-hydroxybenzonitriles 5 and phenacyl bromides 6 via intermediates 7. Similar treatment of 2-sulfanylbenzonitrile (8) provided 3-amino-1-benzothiophenes 3. Appropriately substituted 2-aminobenzonitriles 9 then provided N-substituted 3-aminoindoles 4. 1-(Ethoxycarbonyl)indoles 4e and 4f were successfully deprotected giving indoles 11a and 11b, respectively.