773873-77-1

Usage

Uses

Used in Pharmaceutical Industry:
5-BROMO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER is used as a building block in the synthesis of diverse biologically active compounds. Its structural features and pharmacological properties make it a valuable component in the development of new drugs and pharmaceuticals.
Used in Agrochemical Industry:
5-BROMO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER is used in the synthesis of various agrochemicals. Its versatility and potential applications in this field contribute to the development of new and effective agrochemical products.
Used in Medicinal Chemistry and Drug Discovery:
5-BROMO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER is used as a key intermediate in the synthesis of compounds with potential therapeutic applications. Its unique structural features and pharmacological properties make it a promising candidate for drug discovery and development.
Used in Chemical Research and Development:
5-BROMO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER is used as a versatile substrate for further synthetic modifications in chemical research. Its presence of the bromine atom allows for various chemical reactions and transformations, contributing to the advancement of chemical science and technology.

InChI:InChI=1/C10H8BrNO2/c1-14-10(13)8-5-12-9-3-2-6(11)4-7(8)9/h2-5,12H,1H3

Upstream product

• 67-56-1 methanol 
• 10075-50-0 5-bromo-1H-indole 
• 76-02-8 trifluoroacetyl chloride 
• 10406-06-1 5-bromo-1H-indole-3-carboxylic acid 
• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 586-78-7 para-nitrophenyl bromide 
• 10468-46-9 N-(4-bromophenyl)hydroxylamine 
• 922-67-8 propynoic acid methyl ester 
• 1336879-56-1 2,2,2-trichloro-1-(5-bromo-1H-indol-3-yl)ethan-1-one 
• 1262150-42-4 (Z)-methyl 3-[(4-bromophenyl)amino]acrylate 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 1445963-16-5 1-(3-(9-bromo-2-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-ylamino)propyl)-3-phenylurea 
• 1445963-15-4 methyl 9-bromo-5-methyl-11-(3-(3-phenylureido)propylamino)-5H-indolo[2,3-b]quinoline-2-carboxylate 
• 1421349-51-0 methyl 5-bromo-2-((4-(methoxycarbonyl)phenyl)(methyl)amino)-1H-indole-3-carboxylate 
• 1421349-52-1 methyl 5-bromo-2-((4-chlorophenyl)(methyl)amino)-1H-indole-3-carboxylate 
• 400071-95-6 5-bromo-1-methyl-1H-indole-3-carboxylic acid 
• 163083-67-8 1-Benzyl-5-bromo-1H-indole-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Development and Profiling of Inverse Agonist Tools for the Neuroprotective Transcription Factor Nurr1

The ligand-sensing transcription factor nuclear receptor related 1 (Nurr1) evolves as an appealing target to treat neurodegenerative diseases. Despite its therapeutic potential observed in various rodent models, potent modulators for Nurr1 are lacking as pharmacological tools. Here, we report the structure-activity relationship and systematic optimization of indole-based inverse Nurr1 agonists. Optimized analogues decreased the receptor's intrinsic transcriptional activity by up to more than 90% and revealed preference for inhibiting Nurr1 monomer activity. In orthogonal cell-free settings, we detected displacement of NCoRs and disruption of the Nurr1 homodimer as molecular modes of action. The inverse Nurr1 agonists reduced the expression of Nurr1-regulated genes in T98G cells, and treatment with an inverse Nurr1 agonist mimicked the effect of Nurr1 silencing on interleukin-6 release from LPS-stimulated human astrocytes. The indole-based inverse Nurr1 agonists valuably extend the toolbox of Nurr1 modulators to further probe the role of Nurr1 in neuroinflammation, cancer, and beyond.

Novel Pim Kinase Inhibitor and Uses Thereof

The present invention relates to novel Pim kinase inhibitors and uses thereof. A novel Pim oxydol 1, 3, 4 - (3H) -2 thione (1, 4-2 (3H) Oxadiazole) - based compound having - thione kinase inhibitory activity and a composition for inhibiting Pim kinase or a composition for preventing or treating cancer comprising the same are provided. Since the 1, 3, 4 - oxydol -2 (3H) - thione (1, 4-Oxadiazole-2 (3H) - thione) - based compound of the present invention has a very effective Pim kinase inhibitory activity even at low concentrations, the compound of the present invention can be useful as a composition for preventing or treating cancer through Pim kinase inhibition.

1,3,4-Oxadiazole-2(3H)-thione Analogs as PIM Kinase Inhibitors

Proviral integration site for moloney murine leukemia virus (PIM) kinases are highly expressed in hematological cancers. They phosphorylate downstream substrates that contribute to tumor growth and survival. Therefore, a potent inhibitor of PIM kinases is expected to be effective at treating hematological cancers. In the present study, several indole derivatives of 1,3,4-oxadiazole-2(3H)-thione were synthesized and evaluated as PIM kinase inhibitors. Structure–activity relationship studies yielded potent inhibitors of all three PIM kinases in the single-digit to low double-digit nanomolar IC50 range. Kinase profiling of a representative compound showed high selectivity among 15 other kinases.

Synthesis, anticancer evaluation and molecular docking studies of 2,5-bis(indolyl)-1,3,4-oxadiazoles, Nortopsentin analogues

A series of ten novel 2,5-bis(indolyl)-1,3,4-oxadiazoles were designed and synthesized. All these compounds were evaluated for their cytotoxicity against four cancer cell lines namely A549, MDA-MB-231, MCF-7 and HeLa using MTT reduced assay. Among them, compound 12e exhibited good cytotoxicity on MCF-7 cell line with IC50 value of 1.8 μM and it was identified as a promising drug lead when compared to the standard drug doxorubicin (IC50 value 0.98 μM). Compound, 12h exhibited better antitumor activity against three cancer cell lines i.e., lung (A549), breast (MCF-7) and cervical (HeLa) with IC50 values of 3.3 μM, 2.6 μM and 6.34 μM respectively. The impact of these compounds on colchicine binding site of tubulin polymer was carefully investigated using molecular docking studies and interpretations between actives and inactive were explained.

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

Heteroaromatic Carboxamide Derivatives as Plasma Kallikrein Inhibitors

Heteroaromatic carboxamides of formula (I), wherein Y, R, and X are as defined herein, and pharmaceutically acceptable salts thereof. The compounds of formula (I) can be used in methods for the treatment of diseases which can be influenced by inhibition of plasma kallikrein.

Synthesis, antiproliferative and apoptosis induction potential activities of novel bis(indolyl)hydrazide-hydrazone derivatives

In recent years, indole-indazolyl hydrazide-hydrazone derivatives with strong cell growth inhibition and apoptosis induction characteristics are being strongly screened for their cancer chemo-preventive potential. In the present study, N-methyl and N,N-dimethyl bis(indolyl)hydrazide-hydrazone analog derivatives were designed, synthesized and allowed to evaluate for their anti-proliferative and apoptosis induction potential against cervical (HeLa), breast (MCF-7 and MDA-MB-231) and lung (A549) cancer cell lines relative to normal HEK293 cells. The MTT assay in conjunction with mitochondrial potential assays and the trypan blue dye exclusion were employed to ascertain the effects of the derivatives on the cancer cells. Further, mechanistic studies were conducted on compound 14a to understand the biochemical mechanisms and functional interactions with various signaling pathways triggered in HeLa and MCF-7 cells. Compound 14a induced apoptosis via caspase independent pathway through the participation of mitogen-activated protein kinases (MAPK) such as extracellular signal related kinase (ERK) and p38 as well as p53 pathways. It originates the activation of pro-apoptotic proteins such as Bak and Mcl-1s and also strongly induced the generation of reactive oxygen species. In downstream signaling pathway, activated p53 protein interacted with MAPK pathways, including SAPK/c-Jun N-terminal protein kinase (JNK), p38 and ERK kinases resulting in apoptotic cell death. The involvement of MAPK cascades such as p38, ERK and p38 on compound 14a induced apoptotic cell death was evidenced by the fact that the inclusion of specific inhibitors of p38, ERK1/2 and JNK MAPK (SB2035809, PD98059 and SP600125) prevented the compound 14a towards induced apoptosis. The results clearly showed that MAP kinase cascades were crucial for apoptotic response in compound 14a induced cellular killing and were dependent on p53 activity. Based on the results, compound 14a was identified as a promising candidate for cancer therapeutics and these findings furnish a basis for further in vivo experiments on anti-proliferative activity.

Synthesis, anticancer evaluation and molecular docking studies of bis(indolyl) triazinones, Nortopsentin analogs

Abstract: A new series of bis indolyl tri keto diazo compounds and 3,5-bis(3′-indolyl) triazinones were designed and synthesized as anticancer agents. Their anticancer activity was screened in vitro towards four different human cancer cell lines like HeLa, MCF-7, MDA-MB-231 and A549 cell lines. Among them, compounds 17a and 17b showed potent cytotoxicity with inhibition (IC50) values of 4.6 and 1.3?μM on Human Cervical cancer cell line, respectively. The in silico simulation studies using ADT 1.5.6 tools revealed unique interactions of indole ring of compound 17b with colchicines active site residue Tyr312 could be a valid reason behind its maximum potency when compared to remaining compounds in responsible of its higher activity.

Identification of azepinone fused tetracyclic heterocycles as new chemotypes with protein kinase inhibitory activities

The design and synthesis of small tetracyclic heterocycles which bear two new regioisomeric 2-carboxyethyl-1H-pyrrole-annulated indoloazepinone scaffolds is described. An azepinone motif, which is inherent in the structures of many well studied protein kinase inhibitors, serves as prominent structural feature of the new compounds. Concise access to the new regioisomeric tetracyclic derivatives was accomplished through amide coupling of appropriate pyrrole and indole precursors followed by an intramolecular Heck coupling reaction of the intermediate amide conjugates. Preliminary evaluation of newly synthesized tetracyclic molecules against a panel of protein kinases indicated their inhibitory activities and revealed promising selectivity profiles. The new compounds displayed no significant antiproliferative activity against MCF-7 cancer cells. Interestingly, derivative 19a exhibited selective TAK1 kinase inhibitory activity and figures as a promising chemotype for the discovery of new TAK1 inhibitors.

Amination/Cyclization Cascade by Acid-Catalyzed Activation of Indolenine for the One-Pot Synthesis of Phaitanthrin E

We have developed a concise one-pot synthesis of phaitanthrin E derivatives, where simple starting materials undergo an acid-catalyzed intermolecular amination/intramolecular cyclization cascade.