113577-95-0

Basic information

• Product Name: 1-(2-BROMOETHYL)-5-METHYL-1H-INDOLE-2,3-DIONE
• Synonyms: 1-(2-BROMOETHYL)-5-METHYL-1H-INDOLE-2,3-DIONE
• CAS NO: 113577-95-0
• Molecular Formula: C11H10BrNO2
• Molecular Weight: 268.11
• Mol File: 113577-95-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(2-BROMOETHYL)-5-METHYL-1H-INDOLE-2,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-BROMOETHYL)-5-METHYL-1H-INDOLE-2,3-DIONE(113577-95-0)
• EPA Substance Registry System: 1-(2-BROMOETHYL)-5-METHYL-1H-INDOLE-2,3-DIONE(113577-95-0)

Safety Data

• Hazardous Substances Data: 113577-95-0(Hazardous Substances Data)

Usage

Derivative of

Indole

Heterocycle

Yes

Presence of bromoethyl group

Yes

Presence of methyl group

Yes

Presence of 2,3-dione functional group

Yes

Potential biological activity

Yes

Possible use

Building block in the synthesis of pharmaceuticals or other organic compounds

Safety precautions

Handle with care and in accordance with safe laboratory practices due to potential reactivity and toxicity

Upstream product

• 608-05-9 5-methyl-indole-2,3-dione 
• 106-93-4 ethylene dibromide 

Relevant articles and documents

Isatin-1,2,3-triazole-isatin Scaffolds and Their Antibacterial Activity

Twelve novel isatin-1,2,3-triazole-isatin scaffolds 5a–l were designed, synthesized, and assessed for their in vitro antibacterial activity in this paper. The preliminary results showed that all dimers only endowed with weak antibacterial activity, which was less active than the reference ciprofloxacin. However, the structure–activity relationship was enriched, which may be useful for the further development of more efficient candidates.

1H-1,2,3-Triazole-tethered Isatin–coumarin Hybrids: Design, Synthesis and In Vitro Anti-mycobacterial Evaluation

A series of novel 1H-1,2,3-triazole-tethered isatin–coumarin hybrids 7a–l integrate three anti-tuberculosis bioactive substances/pharmacophoric units including coumarin, isatin, and I-A09 were designed, synthesized, and tested for their in vitro anti-mycobacterial activity against Mycobacterium smegmatis and Mycobacterium tuberculosis H37Rv as well as cytotoxicity in VERO cell line. The results showed that all hybrids exhibited weak to moderate activity against the tested two strains with minimum inhibitory concentration ranging from 50 to 200?μg/mL.

1H-1,2,3-triazole tethered isatin-ferrocene conjugates: Synthesis and in vitro antimalarial evaluation

1H-1,2,3-triazole tethered isatin-ferrocene conjugates were synthesized and evaluated for their antiplasmodial activities against chloroquine-susceptible (3D7) and chloroquine-resistant (W2) strains of Plasmodium falciparum. The conjugates 5f and 5h with an optimum combination of electron-withdrawing halogen substituent at C-5 position of isatin ring and a propyl chain, introduced as linker, proved to be most potent and non-cytotoxic among the series with IC50 values of 3.76 and 4.58 μM against 3D7 and W2 strains, respectively.

Design, Synthesis and In Vitro Anti-mycobacterial Activities of 8-OMe Ciprofloxacin-1H-1,2,3-triazole-isatin-(thio) Semicarbazide/Oxime Hybrids

A series of novel 8-OMe ciprofloxacin (8-OMe CPFX)-1H-1,2,3-triazole-isatin-(thio) semicarbazide/oxime hybrids 6a–l with the capacity to form hydrogen bond were designed, synthesized, and evaluated for their in vitro anti-mycobacterial activities against Mycobacterium tuberculosis (MTB) H37Rv and MDR-TB as well as cytotoxicity. All the synthesized hybrids (MIC: 0.39–16?μg/mL) exhibited excellent activities against MTB H37Rv and MDR-TB, and the majority of them were more potent than the parent 8-OMe CPFX (MIC: 1.56 and 2.0?μg/mL, respectively). In particular, the most active conjugate 6h (MIC: 0.39 and 1.0?μg/mL, respectively) was two to eight times more potent in vitro than the references CPFX (MIC: 3.12 and 4.0?μg/mL, respectively) and 8-OMe CPFX against the tested strains and was comparable with or 64-folds more potent than RIF (MIC: 0.39 and 64?μg/mL, respectively) against MTB H37Rv and MDR-TB, respectively. In addition, all conjugates (CC50: 16–64?μg/mL) showed acceptable cytotoxicity, although most of them were more toxic than the parent (CC50: 64?μg/mL) in VERO cell line.

Azide-alkyne cycloaddition towards 1H-1,2,3-triazole-tethered gatifloxacin and isatin conjugates: Design, synthesis and in?vitro anti-mycobacterial evaluation

Twelve novel 1H-1,2,3-triazole-tethered gatifloxacin (GTFX) isatin conjugates 5a-l with greater lipophilicity compared with GTFX were designed, synthesized and evaluated for their in vitro anti-mycobacterial activities against M. tuberculosis (MTB) H37Rv and MDR-TB as well as cytotoxicity. The preliminary results showed that all the targets (MIC: 0.10–8 μg/mL) exhibited excellent inhibitory activity against MTB H37Rv and MDR-TB, but eight of them (CC50: 7.8–62.5 μg/mL) were much more toxic than the parent GTFX (CC50: 125 μg/mL). Among them, 5g (MIC: 0.10 μg/mL) was 4–8 times more potent in vitro than the references GTFX (MIC: 0.78 μg/mL) and RIF (MIC: 0.39 μg/mL) against MTB H37Rv, but less active than INH (MIC: 0.05 μg/mL). The most potent 5g and 5h (MIC: 0.25 μg/mL) were 4->512 times more active than the three references (MIC: 1.0->128 μg/mL) against MDR-TB. Unfortunately, both of the two hybrids (CC50: 7.8 μg/mL) were much more cytotoxic than the other derivatives, need to be further optimized.

Synthesis of novel 1H-1,2,3-triazole tethered C-5 substituted uracil-isatin conjugates and their cytotoxic evaluation

The present manuscript describes the synthesis of uracil-isatin hybrids via azide-alkyne cycloadditions and their cytotoxic evaluation against three human cancer cell lines viz. HeLa (cervix), MCF-7 (breast) and DU145 (prostate) using MTT assay. The evaluation studies revealed the dependence of cytotoxicity on C-5 substituents of both uracil and isatin as well as the alkyl chain length with compounds 6g and 6k showing IC50 values 18.21 and 13.90 μM respectively against DU145 cell lines. Most of the synthesized conjugates exhibited considerable selectivity against MCF-7 and DU145 cell lines.

Design, synthesis and in vitro anti-mycobacterial evaluation of gatifloxacin-1H-1,2,3-triazole-isatin hybrids

A set of novel gatifloxacin-1H-1,2,3-triazole-isatin hybrids 6a-l was designed, synthesized and evaluated for their in vitro anti-mycobacterial activities against M. tuberculosis (MTB) H37Rv and MDR-TB as well as cytotoxicity. The results showed that all the targets (MIC: 0.025–3.12?μg/mL) exhibited excellent inhibitory activity against MTB H37Rv and MDR-TB, but were much more toxic (CC50: 7.8–62.5?μg/mL) than the parent gatifloxacin (GTFX) (CC50: 125?μg/mL). Among them, 61 (MIC: 0.025?μg/mL) was 2–32 times more potent in vitro than the references INH (MIC: 0.05?μg/mL), GTFX (MIC: 0.78?μg/mL) and RIF (MIC: 0.39?μg/mL) against MTB H37Rv. The most active conjugate 6?k (MIC: 0.06?μg/mL) was 16–>2048 times more potent than the three references (MIC: 1.0–>128?μg/mL) against MDR-TB. Both of the two hybrids warrant further investigations.

Azide-alkyne cycloaddition en route to ferrocenyl-methoxy-methyl-isatin-conjugates: Synthesis, anti-breast cancer activities and molecular docking studies

A series of 1H-1,2,3-triazole linked Ferrocenyl-methoxy-methyl-Isatin conjugates was synthesized and assayed for their anti-proliferative activities against estrogen-responsive as well as estrogen non-responsive cell lines. The non-cytotoxic conjugate 7l, with an optimum combination of octyl chain as spacer and methyl-substituent at the C-5 position of isatin, proved to be a promising hit with an IC50 value of 14.62 μM against MCF-7 and 79.63 μM against MDA-MB-231 cells, respectively. The observed anti-proliferative activities of active conjugates were further corroborated via docking studies carried out on estrogen receptor subtypes α and β.

Isatin-(thio)semicarbazide/oxime-1H-1,2,3-triazole-coumarin Hybrids: Design, Synthesis, and in vitro Anti-mycobacterial Evaluation

Isatin and coumarin derivatives with potential anti-tubercular activity, while (thio)semicarbazide/oxime and 1H-1,2,3-triazole moieties exhibited favorable properties such as hydrogen bonding and/or metal chelation capability, so integration of the four pharmacophores into one molecule may provide more effective anti-tubercular candidates. Based on the consideration earlier, 12 isatin-(thio)semicarbazide/oxime-1H-1,2,3-triazole-coumarin hybrids 8a–l were designed, synthesized, and evaluated for their in vitro anti-mycobacterial activities against M. tuberculosis (MTB) H37Rv and MDR-TB. The results showed that all the hybrids (MIC: 50–>200?μg/mL) exhibited weak to moderate inhibitory activity against MTB H37Rv and MDR-TB, which were far less potent than the references isoniazid (MIC: 0.05?μg/mL) and rifampicin (MIC: 0.39?μg/mL) against MTB H37Rv. The most active hybrid 8h (MIC: 50?μg/mL) was comparable with rifampicin (MIC: 32?μg/mL) and more active than isoniazid (MIC: >128?μg/mL) against MDR-TB, could be act as a lead for further optimization. Moreover, the enriched structure–activity relationship paved the way to the further rational development of this kind of hybrids.

1H-1,2,3-triazole-tethered 8-OMe Ciprofloxacin and Isatin Hybrids: Design, Synthesis and in vitro Anti-mycobacterial Activities

A new class of 1H-1,2,3-triazole-tethered 8-OMe ciprofloxacin (8-OMe CPFX) isatin hybrids 5a–l was designed, synthesized and screened for their in vitro anti-mycobacterial activities against Mycobacterium tuberculosis H37Rv and multi-drug-resistant tuberculosis (MDR-TB). All targets (minimum inhibitory concentration (MIC): 0.20–8.0?μg/mL) exhibited promising inhibitory activity against MTB H37Rv and MDR-TB. Among them, conjugate 5h (MIC: 0.20?μg/mL), was 2–16 times more potent in vitro than the references CPFX (MIC: 3.12?μg/mL), 8-OMe CPFX (MIC: 1.56?μg/mL) and RIF (MIC: 0.39?μg/mL) against MTB H37Rv. The most potent hybrid 5l (MIC: 0.25?μg/mL) was 8–256 times more active than the three references (MIC: 2.0–64?μg/mL) against MDR-TB. Both of them warrant further investigations.