59353-62-7

Basic information

• Product Name: 2-(4-BROMOPENTYL)-1H-ISIONDOLE-1,3(2H)DIONE
• Synonyms: 2-(4-BROMOPENTYL)-1H-ISIONDOLE-1,3(2H)DIONE;2-(4-Bromopentyl)-1H-isoindole-1,3-(2H)dione;2-Bromo-5-phthalimidopentane;2-(4-bromopentyl)isoindole-1,3-dione
• CAS NO: 59353-62-7
• Molecular Formula: C₁₃H₁₄BrNO₂
• Molecular Weight: 296.16
• Product Categories: Amines, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 59353-62-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 386.6°C at 760 mmHg
• Flash Point: 187.6°C
• Appearance: /
• Density: 1.457g/cm³
• Vapor Pressure: 3.5E-06mmHg at 25°C
• Refractive Index: 1.589
• Solubility: DCM, Ethyl Acetate
• PKA: -2.15±0.20(Predicted)
• CAS DataBase Reference: 2-(4-BROMOPENTYL)-1H-ISIONDOLE-1,3(2H)DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-BROMOPENTYL)-1H-ISIONDOLE-1,3(2H)DIONE(59353-62-7)
• EPA Substance Registry System: 2-(4-BROMOPENTYL)-1H-ISIONDOLE-1,3(2H)DIONE(59353-62-7)

Safety Data

• Hazardous Substances Data: 59353-62-7(Hazardous Substances Data)

Usage

Description

2-(4-BROMOPENTYL)-1H-ISIONDOLE-1,3(2H)DIONE is an organic compound with a unique molecular structure that features a 4-bromopentyl group attached to a 1H-isonindole-1,3(2H)dione core. 2-(4-BROMOPENTYL)-1H-ISIONDOLE-1,3(2H)DIONE is characterized by its potential reactivity and versatility in chemical synthesis, making it a valuable intermediate in the production of various pharmaceuticals and other applications.

Uses

Used in Pharmaceutical Synthesis:
2-(4-BROMOPENTYL)-1H-ISIONDOLE-1,3(2H)DIONE is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly those with antimalarial properties. Its unique structure allows for further chemical modifications and functionalization, making it a key component in the development of new drugs.
Used in Antimalarial Applications:
As an intermediate in the synthesis of Primaquine (P733500), 2-(4-BROMOPENTYL)-1H-ISIONDOLE-1,3(2H)DIONE plays a crucial role in the production of an effective antimalarial agent. Primaquine is known for its ability to treat and prevent malaria, particularly in cases where Plasmodium vivax and Plasmodium ovale are involved.
Used in Chemical Research:
2-(4-BROMOPENTYL)-1H-ISIONDOLE-1,3(2H)DIONE is also utilized in chemical research for the exploration of new reactions and the development of novel synthetic methods. Its reactivity and structural features make it an interesting candidate for studying various chemical transformations and understanding the underlying mechanisms.
Used in the Synthesis of Other Compounds:
Due to its unique structure, 2-(4-BROMOPENTYL)-1H-ISIONDOLE-1,3(2H)DIONE can be used as a building block in the synthesis of other complex organic compounds. This allows for the creation of a wide range of molecules with diverse applications, from pharmaceuticals to materials science.

InChI:InChI=1/C13H14BrNO2/c1-9(14)5-4-8-15-12(16)10-6-2-3-7-11(10)13(15)17/h2-3,6-7,9H,4-5,8H2,1H3

Upstream product

• 7736-25-6 2-(pent-4-enyl)-isoindoline-1,3-dione 
• 136918-14-4 phthalimide 
• 16103-56-3 4-bromopentan-1-ol 
• 75411-76-6 methyl 4-bromopentanoate 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 71510-39-9 2-pentyl-1H-isoindole-1,3(2H)-dione 
• 628-17-1 amyl iodide 
• 1074-82-4 potassium phtalimide 
• 626-87-9 1,4-dibromopentane 
• 1119-51-3 bromopentene 

Relevant articles and documents

4,9-Diaminoacridines and 4-Aminoacridines as Dual-Stage Antiplasmodial Hits

Multi-stage drugs have been prioritized in antimalarial drug discovery, as targeting more than one process in the Plasmodium life cycle is likely to increase efficiency, while decreasing the chances of emergence of resistance by the parasite. Herein, we disclose two novel acridine-based families of compounds that combine the structural features of primaquine and chloroquine. Compounds prepared and studied thus far retained the in vitro activity displayed by the parent drugs against the erythrocytic stages of chloroquine-sensitive and -resistant Plasmodium falciparum strains, and against the hepatic stages of Plasmodium berghei, hence acting as dual-stage antiplasmodial hits.

Regiodivergent Conversion of Alkenes to Branched or Linear Alkylpyridines

Herein we report a practical protocol for the visible-light-induced regiodivergent radical hydropyridylation of unactivated alkenes using pyridinium salts. This approach provides a unified synthetic platform to control the regioselectivity of the synthesis of linear or branched C4-alkylated pyridines. A remarkable selectivity switch from the anti-Markovnikov to the Markovnikov product can be achieved by the addition of tetrabutylammonium bromide. The versatility of this protocol is further demonstrated based on the late-stage functionalization in pharmaceuticals.

Endoperoxide-8-aminoquinoline hybrids as dual-stage antimalarial agents with enhanced metabolic stability

Hybrid compounds may play a critical role in the context of the malaria eradication agenda, which will benefit from therapeutic tools active against the symptomatic erythrocytic stage of Plasmodium infection, and also capable of eliminating liver stage parasites. To address the need for efficient multistage antiplasmodial compounds, a small library of 1,2,4,5-tetraoxane-8- aminoquinoline hybrids, with the metabolically labile C-5 position of the 8-aminoquinoline moiety blocked with aryl groups, was synthesized and screened for antiplasmodial activity and metabolic stability. The hybrid compounds inhibited development of intra-erythrocytic forms of the multidrug-resistant Plasmodium falciparum W2 strain, with EC50 values in the nM range, and with low cytotoxicity against mammalian cells. The compounds also inhibited the development of P. berghei liver stage parasites, with the most potent compounds displaying EC50 values in the low μM range. SAR analysis revealed that unbranched linkers between the endoperoxide and 8-aminoquinoline pharmacophores are most beneficial for dual antiplasmodial activity. Importantly, hybrids were significantly more potent than a 1:1 mixture of 8-aminoquinoline-tetraoxane, highlighting the superiority of the hybrid approach over the combination therapy. Furthermore, aryl substituents at C-5 of the 8-aminoquinoline moiety improve the compounds' metabolic stability when compared with their primaquine (i.e. C-5 unsubstituted) counterparts. Overall, this study reveals that blocking the quinoline C-5 position does not result in loss of dual-stage antimalarial activity, and that tetraoxane-8- aminoquinoline hybrids are an attractive approach to achieve elimination of exo- and intraerythrocytic parasites, thus with the potential to be used in malaria eradication campaigns.