3529-82-6

Usage

Uses

Used in Chemical Synthesis:
3-Nitrophenyl isothiocyanate is used as a synthetic building block for the creation of various chemical compounds. It plays a crucial role in the synthesis of different thiourea derivatives and other complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Nitrophenyl isothiocyanate is used as a key intermediate in the synthesis of potential therapeutic agents. It contributes to the development of novel drugs with diverse applications, including the treatment of various diseases and conditions.
Used in the Synthesis of Specific Compounds:
3-Nitrophenyl isothiocyanate is used as a reactant in the synthesis of the following thiourea derivatives:
N-[(3-chlorophenyl)methyl]-N′-(3-nitrophenyl)thiourea
N-[(5-chloro-2-methoxyphenyl)methyl]-N′-(3-nitrophenyl)thiourea
R/S-N-[6-chlorochroman-4-yl]-N′-(3-nitrophenyl)thiourea
These thiourea derivatives have potential applications in various fields, such as agriculture, pharmaceuticals, and materials science, due to their unique chemical properties and reactivity.
Used in the Synthesis of Complex Organic Molecules:
3-Nitrophenyl isothiocyanate is also used in the synthesis of complex organic molecules, such as 2-[(3-nitrophenyl)amino]naphtho[2,1-b]furo-5H-[3,2-d][1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one and 5-methyl-3-(3-nitrophenyl)-2-thiooxazolidin-4-one. These compounds may have potential applications in various industries, including pharmaceuticals, materials science, and chemical research.

InChI:InChI=1/C7H4N2O2S/c10-9(11)7-3-1-2-6(4-7)8-5-12/h1-4H

Upstream product

• 463-71-8 thiophosgene 
• 99-09-2 3-nitro-aniline 
• 3320-87-4 isocyanic acid (3-nitro-phenyl) ester 
• 58655-17-7 m-nitrophenyldithiocarbamic acid triethylamine salt 
• 96989-50-3 di-2-pyridyl thionocarbonate 
• 75-15-0 carbon disulfide 
• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 1414781-31-9 C₇H₆N₂O₂S₂*C₆H₁₂N₂ 
• 86317-32-0 O-(4-methoxyphenyl) N-3-nitrophenylthioncarbamate 
• 13524-85-1 S-<3-Nitro-phenylcarbamoyl>-dithiophosphorsaeure-O,O'-diaethylester 
• 13140-66-4 1-(3-nitrophenyl)-3-phenylthiourea 
• 108-24-7 acetic anhydride 
• 13991-80-5 1,3-bis-(3-nitro-phenyl)-thiourea 
• 64-17-5 ethanol 

Downstream Products

• 108272-32-8 4-(3-nitro-phenyl)-1-(1-oxy-nicotinoyl)-thiosemicarbazide 
• 3700-14-9 (3-nitrophenyl)(trifluoromethyl)carbamic fluoride 
• 62133-89-5 C₁₅H₂₂N₄O₂S 
• 40307-40-2 3-(3-nitrophenyl)-2-thioxothiazolidin-4-one 
• 3549-67-5 <3-Nitro-phenylthiocarbamoyl>-malonsaeure-diaethylester 
• 78721-60-5 4-Phenyl-piperazine-1-carbothioic acid (3-nitro-phenyl)-amide 
• 78721-59-2 4-Benzyl-piperazine-1-carbothioic acid (3-nitro-phenyl)-amide 
• 79865-69-3 2-(2,4-Dinitro-phenyl)-N-(3-nitro-phenyl)-thioacetamide 
• 79865-63-7 2-(2,4-Dinitro-phenyl)-N-(3-nitro-phenyl)-3-oxo-thiobutyramide 
• 78157-94-5 1-(3-Nitro-phenyl)-4,5-dioxo-2-thioxo-pyrrolidine-3-carboxylic acid amide 
• 94772-00-6 C₁₈H₁₈N₈O₅S 
• 139172-38-6 2-(2,4-Dichloro-phenyl)-6-(3-nitro-phenyl)-7-phenyl-6,7-dihydro-[1,3,4]oxadiazolo[3,2-a][1,3,5]triazine-5-thione 

Relevant academic research and scientific papers

4-PHENYL-N-(PHENYL)THIAZOL-2-AMINE DERIVATIVES AND RELATED COMPOUNDS AS ARYL HYDROCARBON RECEPTOR (AHR) AGONISTS FOR THE TREATMENT OF E.G. ANGIOGENESIS IMPLICATED OR INFLAMMATORY DISORDERS

4-phenyl-N-(phenyl)thiazol-2-amine and 4-(pyridin-3-yl)-N-( phenyl) thiazol-2-amine derivatives and the corresponding thiadiazole, thiophene, oxazole, oxadiazole, imidazole and triazole derivatives and related compounds as aryl hydrocarbon receptor (AHR) agonists for the treatment of angiogenesis implicated disorders, such as e.g. retinopathy, psoriasis, rheumatoid arthritis, obesity and cancer, or inflammatory disorders.

Design and synthesis of novel N-[3-(benzimidazol-2-ylamino)phenyl]amine and N-[3-(benzoxazol-2-ylamino)phenyl]amine derivatives as potential anticancer agents

In this contribution, we report the design, synthesis and cytotoxicity studies of a series of N-[3-(benzimidazol-2-yl-amino)phenyl]amine and N-[3-(benzoxazol-2-ylamino)phenyl]amine derivatives. In vitro cytotoxicity assay of 26 selected compounds was carried out at National Cancer Institute (NCI), USA. Out of them, compounds 10e (NSC D-762842/1) and 11s (NSC D-764942/1) have shown remarkable cytotoxicity with GI50 values ranging between “0.589–14.3?μM” and “0.276–12.3?μM,” respectively, in the representative nine subpanels of human tumor cell lines. Further, flow cytometry analysis demonstrated that compound 10e exerted cell cycle arrest at G2/M phase and showed dose-dependent enhancement in apoptosis in K-562 leukemia cancer cells.

Design, synthesis and biological evaluation of novel 2,4-disubstituted quinazoline derivatives targeting H1975 cells via EGFR-PI3K signaling pathway

In order to find new and highly effective anti-tumor drugs with targeted therapeutic effects, a series of novel 4-aminoquinazoline derivatives containing N-phenylacetamide structure were designed, synthesized and evaluated for antitumor activity against four human cancer cell lines (H1975, PC-3, MDA-MB-231 and MGC-803) using MTT assay. The results showed that the compound 19e had the most potent antiproliferative activity against H1975, PC-3, MDA-MB-231 and MGC-803 cell lines. At the same time, compound 19e could significantly inhibit the colony formation and migration of H1975 cells. Compound 19e also arrested the H1975 cell cycle in the G1 phase and mediated cell apoptosis, promoted the accumulation of ROS in H1975 cells. Furthermore, compound 19e exerted antitumor effect in vitro by reducing the expression of anti-apoptotic protein Bcl-2 and increasing the pro-apoptotic protein Bax and p53. Mechanistically, compound 19e could significantly decreased the phosphorylation of EGFR and its downstream protein PI3K in H1975 cells. Which indicated that compound 19e targeted H1975 cell via interfering with EGFR-PI3K signaling pathway. Molecular docking showed that compound 19e could bind into the active pocket of EGFR. Those work suggested that compound 19e would have remarkable implications for further design of anti-tumor agents.

N-Trifluoromethyl Hydrazines, Indoles and Their Derivatives

Reported herein is the first efficient strategy to synthesize a broad range of unsymmetrical N-CF3 hydrazines, which served as platform to unlock numerous currently inaccessible derivatives, such as tri- and tetra-substituted N-CF3 hydrazines, hydrazones, sulfonyl hydrazines, and valuable N-CF3 indoles. These compounds proved to be remarkably robust, being compatible with acids, bases, and a wide range of synthetic manipulations. The feasibility of RN(CF3)-NH2 to function as a directing group in C?H functionalization is also showcased.

Discovery and optimization of 4-oxo-2-thioxo-thiazolidinones as NOD-like receptor (NLR) family, pyrin domain-containing protein 3 (NLRP3) inhibitors

Aberrant activation of NLRP3 inflammasome is present in a subset of acute and chronic inflammatory diseases. The NLRP3 inflammasome has been recognized as an attractive therapeutic target for developing novel and specific anti-inflammatory inhibitors. Cellular structure-activity relationship-guided optimization resulted in the identification of 4-oxo-2-thioxo-thiazolidinone derivative 9 as a selective and direct small-molecule inhibitor of NLRP3 with IC50 of 2.4 μM, possessing favorable ex vivo and in vivo pharmacokinetic properties. Compound 9 may represent a lead for the development of anti-inflammatory therapeutics for treating NLRP3-driven diseases.

Differentiating Antiproliferative and Chemopreventive Modes of Activity for Electron-Deficient Aryl Isothiocyanates against Human MCF-7 Cells

The consumption of Brassica vegetables provides beneficial effects through organic isothiocyanates (ITCs), products of the enzymatic hydrolysis of glucosinolate secondary metabolites. The ITC l-sulforaphane (l-SFN) is the principle agent in broccoli that demonstrates several modes of anticancer action. While the anticancer properties of ITCs like l-SFN have been extensively studied and l-SFN has been the subject of multiple human clinical trials, the scope of this work has largely been limited to those derivatives found in nature. Previous studies have demonstrated that structural changes in an ITC can lead to marked differences in a compound's potency to 1) inhibit the growth of cancer cells, and 2) alter cellular transcriptional profiles. This study describes the preparation of a library of non-natural aryl ITCs and the development of a bifurcated screening approach to evaluate the dose- and time-dependence on antiproliferative and chemopreventive properties against human MCF-7 breast cancer cells. Antiproliferative effects were evaluated using a commercial MTS cell viability assay. Chemopreventive properties were evaluated using an antioxidant response element (ARE)-promoted luciferase reporter assay. The results of this study have led to the identification of 1) several key structure–activity relationships and 2) lead ITCs for continued development.

Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water

We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.

Inhibitors of the Diadenosine Tetraphosphate Phosphorylase Rv2613c of Mycobacterium tuberculosis

The intracellular concentration of diadenosine tetraphospate (Ap4A) increases upon exposure to stress conditions. Despite being discovered over 50 years ago, the cellular functions of Ap4A are still enigmatic. If and how the varied Ap4A is a signal and involved in the signaling pathways leading to an appropriate cellular response remain to be discovered. Because the turnover of Ap4A by Ap4A cleaving enzymes is rapid, small molecule inhibitors for these enzymes would provide tools for the more detailed study of the role of Ap4A. Here, we describe the development of a high-throughput screening assay based on a fluorogenic Ap4A substrate for the identification and optimization of small molecule inhibitors for Ap4A cleaving enzymes. As proof-of-concept we screened a library of over 42, 000 compounds toward their inhibitory activity against the Ap4A phosphorylase (Rv2613c) of Mycobacterium tuberculosis (Mtb). A sulfanylacrylonitril derivative with an IC50 of 260 ± 50 nM in vitro was identified. Multiple derivatives were synthesized to further optimize their properties with respect to their in vitro IC50 values and their cytotoxicity against human cells (HeLa). In addition, we selected two hits to study their antimycobacterial activity against virulent Mtb to show that they might be candidates for further development of antimycobacterial agents against multidrug-resistant Mtb.

Terminal functionalized thiourea-containing dipeptides as multidrug-resistance reversers that target 20S proteasome and cell proliferation

A series of inhibitors of 20S proteasome based on terminal functionalized dipeptide derivatives containing the thiourea moiety were synthesized and evaluated for inhibition of 20S proteasome and the effects of multidrug-resistance reversers. These compounds exhibited significant selectivity to the β5-subunit of the human 20S proteasome with IC50values at submicromolar concentrations. A docking study of the most active compound 6i revealed key interactions between 6i and the active site of the 20S proteasome in which the thiourea moiety and a nitro group were important for improving activity. In particular, compound 6i appeared to be the most potent compound against the NCI-H460 cell line, and displayed similar efficiency in drug-sensitive versus drug-resistant cancer cell lines, at least partly, by inhibition of the activity of 20S proteasome and induce apoptosis. In addition, 6i-induced apoptosis was significantly facilitated in NCI-H460/DOX cells that had been pretreated with inhibitors of P-gp. Mechanistically, compound 6i might trigger apoptotic signalling pathway. Thus, we conclude that dipeptide derivatives containing the thiourea moiety may be the potential inhibitors of proteasome with the ability to reverse multidrug resistance.

Synthesis and biological evaluation of terminal functionalized thiourea-containing dipeptides as antitumor agents

A series of antitumor agents based on terminal functionalized dipeptide derivatives containing the thiourea moiety were synthesized and evaluated for antiproliferative activity using a panel of cancer cell lines, and the effects and mechanism of apoptosis induction were determined. These compounds exhibited significant selectivity to different cancer cell lines with IC50 values at micromolar concentrations. In particular, compound I-11 appeared to be the most potent compound, with an IC50 = 4.85 ± 1.44 μM against the NCI-H460 cell line, at least partly, by the induction of apoptosis. Mechanistically, compound I-11 induced the activation of caspase-12 and CHOP, which triggered apoptotic signalling via the ROS-dependent endoplasmic reticulum pathway and arrested the cell cycle at the S phase. Thus, we concluded that dipeptide derivatives containing the thiourea moiety terminally functionalized by electron-withdrawing substituents may be potential antitumor agents for further investigation.