3414-64-0

Usage

Uses

Used in Organic Synthesis:
5-NITROGRAMINE is used as a synthetic building block for the creation of various organic compounds. Its chemical structure allows it to be a versatile component in the synthesis of a wide range of molecules, making it valuable in the field of organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-NITROGRAMINE is used as an intermediate in the synthesis of various drugs and pharmaceutical compounds. Its unique chemical properties enable the development of new medications with potential therapeutic applications.
Used in Chemical Research:
5-NITROGRAMINE is also utilized in chemical research as a model compound to study various chemical reactions and mechanisms. This helps researchers gain a better understanding of the underlying principles of organic chemistry and potentially discover new synthetic pathways or applications for the compound.

InChI:InChI=1/C11H13N3O2/c1-13(2)7-8-6-12-11-4-3-9(14(15)16)5-10(8)11/h3-6,12H,7H2,1-2H3

Upstream product

• 50-00-0 formaldehyd 
• 6146-52-7 5-nitroindole 
• 124-40-3 dimethyl amine 
• 33797-51-2 eschenmoser's salt 
• 6625-96-3 5-nitro-1H-indole-3-carbaldehyde 

Downstream Products

• 6952-13-2 <5-Nitro-indolyl-(3)>-acetonitril 
• 131195-98-7 3-(methoxymethyl)-5-nitro-1H-indole 
• 6625-96-3 5-nitro-1H-indole-3-carbaldehyde 
• 3414-74-2 N,N-dimethyl-1-(5-amino-1H-indol-3-yl)methanamine 
• 6525-46-8 5-nitro-DL-tryptophan 
• 6958-33-4 diethyl acetylamino<(5-nitroindol)-3-ylmethyl>malonate 

Relevant academic research and scientific papers

Discovery of IDO1 and DNA dual targeting antitumor agents

The development of small molecules for cancer immunotherapy is highly challenging and indoleamine 2,3-dioxygenase 1 (IDO1) represents a promising target. Inspired by the synergistic effects between IDO1 inhibitors and traditional antitumor chemotherapeutics, the first orally active dual IDO1 and DNA targeting agents were designed by the pharmacophore fusion strategy. The bifunctional hybrids exhibited enhanced IDO1 enzyme inhibitory activity and in vitro cytotoxicity as compared to IDO1 inhibitor 1-methyl-tryptophan and DNA alkylating agent melphalan. In a murine LLC tumor model, the dual targeting agents demonstrated excellent antitumor efficacy, highlighting the advantages of this novel design strategy to improve the efficacy of small molecule cancer immunotherapy.

Synthesis and in Vitro Evaluation of Novel 5-Nitroindole Derivatives as c-Myc G-Quadruplex Binders with Anticancer Activity

Lead-optimization strategies for compounds targeting c-Myc G-quadruplex (G4) DNA are being pursued to develop anticancer drugs. Here, we investigate the structure-activity- relationship (SAR) of a newly synthesized series of molecules based on the pyrrolidine-substituted 5-nitro indole scaffold to target G4 DNA. Our synthesized series allows modulation of flexible elements with a structurally preserved scaffold. Biological and biophysical analyses illustrate that substituted 5-nitroindole scaffolds bind to the c-Myc promoter G-quadruplex. These compounds downregulate c-Myc expression and induce cell-cycle arrest in the sub-G1/G1 phase in cancer cells. They further increase the concentration of intracellular reactive oxygen species. NMR spectra show that three of the newly synthesized compounds interact with the terminal G-quartets (5′- and 3′-ends) in a 2 : 1 stoichiometry.

Rhodium-Catalyzed Enantioselective Cyclization of 3-Allenyl-indoles: Access to Functionalized Tetrahydrocarbazoles

A highly selective rhodium-catalyzed cyclization of tethered 3-allenylindoles is reported. In a smooth reaction, 1-vinyltetrahydrocarbazoles are obtained in excellent yields and enantioselectivities. Aside from a great functional group tolerance, this method requires neither the Schlenk technique nor the use of anhydrous solvents. Preliminary mechanistic investigations proved that the reaction proceeds via an intermediary formed spiroindolenine which rapidly undergoes an acid-catalyzed stereospecific migration.

Rhodium-Catalyzed Diastereo- And Enantioselective Tandem Spirocyclization/Reduction of 3-Allenylindoles: Access to Functionalized Vinylic Spiroindolines

A highly selective rhodium-catalyzed tandem spirocyclization/reduction of 3-allenylindoles is reported. By employing a Hantzsch ester as reductant, vinylic spiroindolines are obtained in excellent yields as well as diastereo- and enantioselectivity. In addition, the reaction's synthetic utility is highlighted by broad functional group compatibility and exemplified by a gram scale reaction with subsequent assorted transformations.

Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131)

Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI50 1.5 μM). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20 mg/kg IP twice a day.

Novel methyl indolinone-6-carboxylates containing an indole moiety as angiokinase inhibitors

A novel series of methyl indolinone-6-carboxylates bearing an indole moiety were identified as potent angiokinase inhibitors. The most active compound, A8, potently targeted the kinase activities of vascular endothelial growth factor receptors 2 and 3, and platelet-derived growth factor receptors α and β, with IC50 values in the nanomolar range. In addition, A8 effectively suppressed the proliferation of human umbilical vein endothelial cells, and HT-29 and MCF-7 cancer cells, by inducing apoptosis. Compound A8 is thus a promising candidate for further investigation.

Ru-catalysed C-H silylation of unprotected gramines, tryptamines and their congeners

Selective Ru-catalysed C2-H silylation of heteroarenes is presented. The transformation works with or without directing group assistance and requires no protecting groups. Gramines and tryptamines may be converted efficiently whilst avoiding deleterious elimination side-reactions. Mechanistic studies reveal an unusual activation of the indole C4-H bond by an electron-rich metal.

Mild microwave-assisted synthesis of dipyrromethanes and their analogues

The Mannich reaction between pyrroles or indoles and Eschenmoser's salt (dimethylmethylideneammonium iodide) forms N,N-dimethylamino-methylated derivatives in good to excellent yields. The reaction is highly regioselective, and for pyrroles both 2-and 3-s

Synthesis and NMR characteristics of N-acetyl-4-nitro, N-acetyl-5-nitro, N-acetyl-6-nitro and N-acetyl-7-nitrotryptophan methyl esters

N-acetyl-4-nitrotryptophan methyl ester (2), N-acetyl-5-nitrotryptophan methyl ester (3), N-acetyl-6-nitrotryptophan methyl ester (4) and N-acetyl-7-nitrotryptophan methyl ester (5) were synthesized through a modified malonic ester reaction of the appropriate nitrogramine analogs followed by methylation with BF3-methanol. Assignments of the 1H and 13C NMR chemical shifts were made using a combination of 1H-1H COSY, 1H-13C HETCOR and 1H-13C selective INEPT experiments. Copyright