23126-68-3

Basic information

• Product Name: 6-aminobenzo[1,3]dioxole-5-carbaldehyde
• Synonyms: 6-aminobenzo[1,3]dioxole-5-carbaldehyde;6-Amino-1,3-benzodioxole-5-carbaldehyde;6-aminopiperonal6-aminobenzo[d][1,3]dioxole-5-carbaldehyde
• CAS NO: 23126-68-3
• Molecular Formula: C₈H₇NO₃
• Molecular Weight: 165.15
• Mol File: 23126-68-3.mol
• Article Data: 24

Chemical Properties

• Melting Point: 107 °C
• Boiling Point: 348.5°Cat760mmHg
• Flash Point: 214.1°C
• Appearance: /
• Density: 1.441g/cm³
• Vapor Pressure: 5.02E-05mmHg at 25°C
• Refractive Index: 1.682
• PKA: 0.65±0.20(Predicted)
• CAS DataBase Reference: 6-aminobenzo[1,3]dioxole-5-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 6-aminobenzo[1,3]dioxole-5-carbaldehyde(23126-68-3)
• EPA Substance Registry System: 6-aminobenzo[1,3]dioxole-5-carbaldehyde(23126-68-3)

Safety Data

• Hazardous Substances Data: 23126-68-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H7NO3/c9-6-2-8-7(11-4-12-8)1-5(6)3-10/h1-3H,4,9H2

Upstream product

• 712-97-0 6-nitro-1,3-benzodioxole-5-carbaldehyde 
• 120-57-0 piperonal 

Downstream Products

• 79835-12-4 2-acetylamino-4,5-methylenedioxybenzaldehyde 
• 28231-30-3 3-((E)-6-amino-benzo[1,3]dioxol-5-ylmethylene)-1-phenyl-pyrrolidine-2,5-dione 
• 34086-69-6 6,7-Methylendioxypyrrolochinolin (19) 
• 28200-02-4 3-((E)-6-amino-benzo[1,3]dioxol-5-ylmethylene)-1-(4-methoxy-phenyl)-pyrrolidine-2,5-dione 
• 28202-80-4 1-(4-acetyl-phenyl)-3-((E)-6-amino-benzo[1,3]dioxol-5-ylmethylene)-pyrrolidine-2,5-dione 
• 76787-29-6 6-(2-nitro-4,5-dimethoxyphenyl)<1,3>dioxolo<4,5-g>quinoline 
• 104155-89-7 10,11-(methylenedioxy)-(20RS)-camptothecin 
• 151636-76-9 10,11-(methylenedioxy)-(20R)-camptothecin 
• 55149-47-8 6-amino-1,3-dioxolo<4,5-g>quinoline-7-carboxamide 
• 57489-86-8 6,7-(methylenedioxy)-2-phenylquinoline 
• 20332-16-5 4,5-methylenedioxyanthranilic acid 
• 89967-41-9 4-phenyl-8,9-methylenedioxy-1,4,5-benzotriazocin-2(1H)-one hydrochloride 
• 89967-43-1 4-(m-methylphenyl)-8,9-methylenedioxy-1,4,5-benzotriazocin-2(1H)-one hydrochloride 
• 89967-42-0 4-(p-methylphenyl)-8,9-methylenedioxy-1,4,5-benzotriazocin-2(1H)-one hydrochloride 

Relevant articles and documents

Antitumor activity of FL118, a survivin, Mcl-1, XIAP, and cIAP2 selective inhibitor, is highly dependent on its primary structure and steric configuration

We recently reported the identification and characterization of a novel small chemical molecule designated FL118. FL118 selectively inhibits multiple cancer survival and proliferation-associated antiapoptotic proteins (survivin, Mcl-1, XIAP, cIAP2) and eliminates small and large human tumor xenografts in animal models (Ling et al., PLoS One 2012, 7, e45571). Here, we report a follow-up study on the structure-activity relationship (SAR) of the hydroxyl group in the lactone ring of FL118. We found that the superior antitumor efficacy of FL118 heavily depends on its steric configuration through comparing the antitumor activity of FL118 with FL113 (the racemic mixture of FL118). Consistently, FL118 proved much more effective in inhibiting the expression of survivin, Mcl-1, and cIAP2, both in vitro and in vivo, compared to FL113. Additionally, Tet-on controlled induction of survivin or forced expression of Mcl-1 protects cancer cells from FL118-mediated growth inhibition and cell death. To further explore the SAR, we synthesized seven position 20-esterifiable FL118 and FL113 derivatives. Studies on these seven new compounds revealed that keeping a free hydroxyl group of FL118 is also important for high antitumor efficacy. Together, these studies confirm the superior anticancer activity of FL118 and narrow the window for further SAR studies to generate novel analogues based on FL118 core structure on its other potential chemical positions.

Piperidine compound and preparation method and medical application thereof

The invention discloses a piperidine compound shown as a formula (I) and a preparation method and medical application thereof, and particularly relates to a piperidine USP7 inhibitor compound or pharmaceutically acceptable salt or ester or solvate thereof and a preparation method and application of the piperidine USP7 inhibitor compound or pharmaceutically acceptable salt or ester or solvate thereof. The compound provided by the invention can inhibit the activity of USP7 enzyme, has very good selectivity and druggability, and can be used for preparing medicines for preventing or treating tumor diseases or virus infectious diseases.

Self-assembling nanoparticles of dually hydrophobic prodrugs constructed from camptothecin analogue for cancer therapy

Nanomedicines have shown success in cancer therapy in recent years because of their excellent solubility in aqueous solution and drug accumulation through controlled release in tumor tissues, but the preparation of most nanomedicines still requires ionic materials, surfactants or the amphiphilic structure to maintain nanoparticle stability and function. In this study, we developed a couple of novel dually hydrophobic prodrugs (DHPs) by combining two hydrophobic compounds through different linkers and elaborated their self-assembly mechanisms by virtue of computational simulation. Importantly, without using any excipients, FL-2 NPs exhibited significantly prolonged retention in blood circulation and displayed a remarkable anti-tumor effect at very low concentration in vivo. Both DHPs consisted of camptothecin structural analogue(FL118) and a marine natural product (ES-285). Comparative experiments proved that these compounds could quickly form nanoparticles by way of simple preparation and remained relatively stable for long periods in PBS. FL-2 NPs linked with a disulphide bond could rapidly release bioactive FL118 after being triggered by endogenous reductive stimulus to exert anti-cancer effects. Overall, this study provides a new strategy for design of therapeutic nanomedicines consisting of dually hydrophobic molecules for cancer therapy.