40830-68-0

Usage

Uses

Used in Pharmaceutical Industry:
SN-38 is used as an active metabolite in cancer treatment for its topoisomerase I inhibitory properties. It is particularly effective against various types of cancer due to its ability to cause DNA damage and induce cell death.
Used in Anticancer Applications:
SN-38 is employed as an anticancer agent, targeting a wide range of malignancies. Its mechanism of action involves inhibiting topoisomerase I, leading to DNA damage and cell death. This makes it a promising candidate for the treatment of various cancers.
Used in Drug Delivery Systems:
To enhance the efficacy and bioavailability of SN-38, researchers have developed novel drug delivery systems. These systems utilize organic and metallic nanoparticles as carriers for SN-38, aiming to improve its delivery and therapeutic outcomes in cancer treatment.
Used in Treatment of Inflammatory Disorders and Infectious Diseases:
SN-38 has been studied for its potential to treat other conditions beyond cancer, such as inflammatory disorders and infectious diseases. Its mechanism of action and potency make it a candidate for further research and development in these areas.

InChI:InChI=1/C16H16N2O4/c19-11-15(17-10-12-4-2-1-3-5-12)16(20)13-6-8-14(9-7-13)18(21)22/h1-10,15-16,19-20H,11H2/b17-10+/t15-,16-/m0/s1

Upstream product

• 119-62-0 (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol 
• 116975-43-0 1-(4-nitro-phenyl)-3,5-diphenyl-dihydro-oxazolo[3,4-c]oxazole 
• 119-62-0 (1RS,2SR)-2-amino-1-(4-nitro-phenyl)-propane-1,3-diol 
• 100-52-7 benzaldehyde 
• 119-62-0 (+/-)-threo-1-(4-nitro-phenyl)-2-amino-1,3-propanediol 
• 109694-51-1 (2Ξ,4RS)-4-((RS)-α-acetoxy-4-nitro-benzyl)-3-acetyl-2-(3-nitro-phenyl)-oxazolidine 
• 119-62-0 2-amino-1-(4-nitrophenyl)propane-1,3-diol 

Downstream Products

• 666236-62-0 (1S,2S)-2-(N-benzyl-N-methylamino)-3-(p-nitrophenyl)propane-1,3-diol 
• 56-75-7 chlorampenicol 
• 255911-56-9 (+)-(4S,5S)-3-benzyl-4-hydroxymethyl-5-(4-nitrophenyl)oxazolidine 
• 255911-55-8 (1S,2S)-2-benzylamino-1-(4-nitrophenyl)-1,3-propanediol 

Relevant academic research and scientific papers

Catalytic asymmetric transfer hydrogenation/dynamic kinetic resolution: an efficient synthesis of florfenicol

A robust and practical method has been developed for the synthesis of florfenicol (1) starting from commercial available 4-(methylsulfonyl) benzoic acid. The key step in this synthesis was the Ru-chloramphenicol base catalyzed asymmetric transfer hydrogenation of N-Boc α-amino-β-ketoester 5 through a dynamic kinetic resolution, which afforded the key chiral building block, anti-(2S,3S)-α-Boc-amino-β-hydroxyl ester 4, with high diastereoselectivity (92% de) and enantioselectivity (78% ee). The synthesis of a series of novel chloramphenicol base ligands L1–L10 is also included. This protocol could also be used for the asymmetric synthesis of fully synthetic analogs of florfenicol.

Highly Enantioselective Construction of a Chiral Tertiary Carbon Center by Alkynylation of a Cyclic N-Acyl Ketimine: An Efficient Preparation of HIV Therapeutics

Second-generation nonnucleoside reverse transcriptase inhibitors can now be efficiently prepared. Alkynylation of the ketimine (see scheme; PMB=p-methoxybenzyl) leads to the synthesis of tertiary amines in excellent yield and with high enantioselectivity. The ligand used in the reaction is a derivative of chloramphenicol base.

Regioselectivity in the reaction of paraformaldehyde with (1S,2S)-2-aryl(hetaryl)methylamino-1-(4-nitrophenyl)-13-propanediols

The reaction of paraformaldehyde with (1S,2S)-2-aryl(hetaryl)methylamino-1-(4-nitrophenyl)-1,3-propanediols produces a mixture of isomeric 3-aryl(hetaryl)methyl-4-hydroxymethyl-5-(4-nitrophenyl)-and 3-aryl(hetaryl)methyl-4-hydroxy(4-nitrophenyl)methyloxazolidines and is reversible. 1999 KluwerAcademic/Plenum Publishers.

Heterocyclic Saturated Compounds (1,3-Dioxanes and Oxazolidynes) by Diastereospecific Closure of threo-1-Amino-1-(4-nitrophenyl)-propane-1,3-diol. I

The reaction involving a diastereospecific closure of threo-2-amino-1-(4-nitrophenyl)-propane-1,3-diol with certain aldehydes was investigated; besides synthetic aspects, those which refer to stereochemical details are also discussed, mainly based on 1H-NMR studies.

SYNTHESIS AND CHIRAL-OPTICAL CHARACTERISTICS OF SCHIFF BASES FROM (+)-THREO-1-(4-NITROPHENYL)-2-AMINO-1,3-PROPANEDIOL

A series of Schiff bases were synthesized from (+)-threo-1-(4-nitrophenyl)-2-amino-1,3-propanediol with substituted benzaldehydes.The Schiff bases from benzaldehyde and para-substituted benzaldehydes give analogous circular dichroism spectra with negative Cotton effects in the regions of 350, 250, and 220 nm and a positive Cotton effect in the region of 270 nm.The positive Cotton effect is due to the interaction of the aromatic chromophores (4-NO2C6H4- and Ar-CH=N-), which form a right-handed spiral in one of the preferred conformations.