23153-09-5

Usage

Uses

Used in Dye and Pigment Production:
4-(Methylsulfanyl)-2-nitroaniline is used as a key intermediate in the synthesis of various dyes and pigments for different applications. Its chemical properties and yellow crystalline nature contribute to the color characteristics of the final products.
Used in Chemical Research:
In the field of chemical research, 4-(Methylsulfanyl)-2-nitroaniline serves as a valuable compound for studying the properties and reactions of aromatic amines and sulfanyl groups. It can be used to explore new chemical pathways and develop innovative applications in various industries.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, given its chemical structure, 4-(Methylsulfanyl)-2-nitroaniline could potentially be used in the pharmaceutical industry as a building block for the development of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Analytical Chemistry:
4-(Methylsulfanyl)-2-nitroaniline, due to its distinct chemical properties, can be employed in analytical chemistry as a reagent or indicator in various assays and tests, helping to identify or quantify specific substances.

InChI:InChI=1/C7H8N2O2S/c1-12-5-2-3-6(8)7(4-5)9(10)11/h2-4H,8H2,1H3

Upstream product

• 2524-76-7 1-(methylsulfanyl)-3-nitrobenzene 
• 54029-45-7 2-nitro-4-thiocyanoaniline 
• 74-88-4 methyl iodide 
• 13511-86-9 S-(3-nitrophenyl) dimethylthiocarbamate 
• 3814-18-4 3-nitrothiophenol 
• 54029-46-8 acetic acid-(2-nitro-4-thiocyanato-anilide) 

Downstream Products

• 21731-56-6 1-Amino-4-methylsulphonyl-2-nitrobenzene 
• 61325-11-9 3-(4-Methylthio-2-nitroanilino)-thiophene-4-nitrile 
• 21731-57-7 5-methylsulphonyl-1,2-phenylenediamine 
• 251462-44-9 4-methylmercapto-2-nitrophenyl azide 
• 61325-09-5 3-(4-Methylthio-2-nitroanilino)-2,5-dihydrothiophene-4-nitrile 

Relevant academic research and scientific papers

Structure-activity relationships of 1,2,4-benzotriazine 1,4-dioxides as hypoxia-selective analogues of tirapazamine

Tirapazamine (TPZ, 1,2,4-benzotriazin-3-amine 1,4-dioxide) is a bioreductive hypoxic cytotoxin currently in Phase II/III clinical trials in combination with radiotherapy and with cisplatin-based chemotherapy. As part of a program to develop TPZ analogues with improved solubility/potency and therapeutic indices, we synthesized 34 1,2,4-benzotriazin-3-amine 1,4-dioxides (BTO) to examine structure-activity relationships (SAR) for ring substitution. The electronic, hydrophobic, and steric parameters of substituents at the 5-, 6-, 7-, and 8-positions were systematically varied, and the aqueous solubility and one-electron reduction potentials [E(1)] of the analogues were determined. For each compound, we determined cell killing of mouse SCCVII tumor cells in vitro under aerobic and hypoxic conditions by clonogenic survival and determined their relative hypoxic toxicity (RHT; relative to TPZ) and hypoxic cytotoxicity ratio (HCR). A subset of compounds was independently evaluated using a 96-well SRB proliferation assay, the data from which correlated well with that derived by the clonogenic endpoint. Most substituents, except 5- and 8-dimethylamino and 8-diethylamino, gave analogues less soluble than TPZ. E(1) values ranged from -240 mV through -670 mV (with TPZ having a value of -456 mV) and correlated well with the electronic parameter σ for substituents at the 5-, 6-, 7-, and 8-positions. Aerobic cytotoxic potency showed a strong positive correlation with E(1) (i.e., electron-withdrawing substituents increased aerobic toxicity). Hypoxic cytotoxicity also generally increased with increasing E(1), with a maximum (RHT up to 3.9-fold) seen in halo- and trifluoromethyl-substituted BTO derivatives having E(1) between ca. -370 to -400 mV. Analogues with high HCRs (>50) all had E(1)s in the range -450 to -510 mV (weakly electron-donating substituents) with the exception of the 8-CF3 analogue, which had an HCR of 112 against SCCVII despite a high E(1) of -372 mV). The results suggest that ring-A substituents in BTO analogues can be used to predictably vary one-electron reduction potentials and also provide a much better definition than previously of the optimum range of these reduction potentials for a desirable biological activity profile (high HCR, RHT, and solubility).

Benzofuroxan derivatives, their therapeutic uses and pharmaceutical compositions

The invention discloses use of a compound of the benzofuroxan series for treatment of cardiovascular disorders represented by the general formula (I) and pharmaceutically acceptable salts thereof wherein: R is halogen, acetoxy, —X—R′, —C(O)NR″R′″, or —C(O

Substituted (alkoxycarbonylthioureido)-(acylamino)-benzene derivatives

Benzene derivatives of the formula: STR1 wherein R1 represents alkyl, R2 represents a group --SR3, --SOR3, --SO2 R3, --OR3, --SCONH2, --SCN or --T(CH2)m T1 R4 [wherein R3 represeents alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, unsubstituted or substituted aryl, or cycloalkylalkyl, R4 represents hydrogen or alkyl, T and T1 each represent oxygen, sulphur or sulphinyl, and m is an integer from 1 to 7] whose position on the benzene ring is either para to the group --NHCSNHCOOR1 or para to the group --NHCOAZ, A represents a bivalent straight-chain aliphatic hydrocarbon radical of 1 to 4 carbon atoms or a said hydrocarbon radical substituted by at least one methyl group, and Z represents a group of the formula:- STR2 wherein R5 represents hydrogen or alkyl, R6 represents hydrogen, alkyl or phenylalkyl, and R7 represents hydrogen or alkyl, or R6 and R7 together with the nitrogen atom to which they are attached form a 5-,6- or 7-membered heterocyclic ring optionally substituted by alkyl group(s), and X- represents a pharmaceutically acceptable anion, are new compounds useful as anthelmintics and antifungal agents.