4357-96-4

Usage

Uses

Used in Pharmaceutical Industry:
AMINO[(4-NITROBENZYL)SULFANYL]METHANIMINIUM CHLORIDE is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs with specific therapeutic properties.
Used in Research and Development:
In the field of research and development, AMINO[(4-NITROBENZYL)SULFANYL]METHANIMINIUM CHLORIDE is used as a reagent for the preparation of indoleamine dioxygenase and the study of structure-activity relationships (SAR) of benzylisothiourea derivatives. This helps researchers understand the interactions between these compounds and their biological targets, leading to the development of more effective drugs.
Used in Chemical Synthesis:
AMINO[(4-NITROBENZYL)SULFANYL]METHANIMINIUM CHLORIDE is also used as a building block in the synthesis of various organic compounds. Its versatile structure allows it to be incorporated into a wide range of molecules, making it a valuable tool for chemists working on the development of new materials and chemicals.

InChI:InChI=1/C8H9N3O2S.ClH/c9-8(10)14-5-6-1-3-7(4-2-6)11(12)13;/h1-4H,5H2,(H3,9,10);1H

Upstream product

• 100-14-1 4-nitrobenzyl chloride 
• 17356-08-0 thiourea 
• 619-73-8 4-nitrobenzyl chloride 

Downstream Products

• 6310-10-7 4-nitrobenzaldehyde hydrazone 
• 39549-05-8 bis(4-nitrobenzyl)disulfide 
• 26798-33-4 (p-nitrophenyl)methanethiol 

Relevant academic research and scientific papers

Novel and highly efficient synthesis of 3-(alkyl/benzylthio)-9b-hydroxy-1H-imidazo[5,1-a]isoindole-1,5(9bH)-dione derivatives

The oxidation of 3a,8a-dihydroxy-2-(alkyl/benzylthio)indeno[1,2-d]imidazol-8(3H)-ones to give the corresponding 3-(alkyl/benzylthio)-9b-hydroxy-1H-imidazo[5,1-a]isoindole-1,5(9bH)-dione derivatives in good to excellent yields at room temperature using two oxidants, periodic acid in aqueous ethanol and lead(IV) acetate in acetic acid, has been reported.

Degradation of MAC13243 and studies of the interaction of resulting thiourea compounds with the lipoprotein targeting chaperone LolA

The discovery of novel small molecules that function as antibacterial agents or cellular probes of biology is hindered by our limited understanding of bacterial physiology and our ability to assign mechanism of action. We previously employed a chemical genomic strategy to identify a novel small molecule, MAC13243, as a likely inhibitor of the bacterial lipoprotein targeting chaperone, LolA. Here, we report on the degradation of MAC13243 into the active species, S-(4-chlorobenzyl)isothiourea. Analogs of this compound (e.g., A22) have previously been characterized as inhibitors of the bacterial actin-like protein, MreB. Herein, we demonstrate that the antibacterial activity of MAC13243 and the thiourea compounds are similar; these activities are suppressed or sensitized in response to increases or decreases of LolA copy number, respectively. We provide STD NMR data which confirms a physical interaction between LolA and the thiourea degradation product of MAC13243, with a K d of ～150 μM. Taken together, we conclude that the thiourea series of compounds share a similar cellular mechanism that includes interaction with LolA in addition to the well-characterized target MreB.

Synthesis and antimicrobial and nitric oxide synthase inhibitory activities of novel isothiourea derivatives

The reaction of substituted benzylhalides, or of halomethyl derivatives of thiophene or furane, with thiourea or its derivatives yielded the respective isothioureas as hydrohalide salts. The products (a total of 17, including 16 novel compounds) were test

INHIBITION OF CELL PROLIFERATION

The disclosed modulators of Rb:Raf-1 interactions are potent, selective disruptors of Rb:Raf-1 binding, with IC50 values ranging from 80 nM to 500 nM. Further, these compounds are surprisingly effective in inhibiting a wide variety of cancer cells, including osteosarcoma, epithelial lung carcinoma, non small cell lung carcinoma, three different pancreatic cancer cell lines, two different glioblastoma cell lines, metastatic breast cancer, melanoma, and prostate cancer. Moreover, the disclosed compounds effectively disrupt angiogenesis and significantly inhibited tumors in nude mice derived from human epithelial lung carcinoma tumors. Accordingly, the disclosed compounds, pharmaceutical compositions comprising the compounds, methods of inhibiting cell proliferation, methods of treating subjects with cancer, and methods of preparing the disclosed compounds are provided.

Nucleophilic Substitution Reaction of Phenylmethanesulfonyl Halides with Anilines

Kinetic studies on the nucleophilic substitution reaction of Y-substituted phenylmethanesulfonyl halides with X-substituted anilines in methanol-acetonitrile have been carried out in order to elucidate the reaction mechanism.The phenylmethanesulfonyl fluorides (PSF) had markedly lower rates and smaller magnitudes of ρX and ρY values compared with those for the chlorides (PSC).On the contrary, however, the magnitude of the cross-interaction constant ρXY was greater for PSF than for PSC, so that the degree of bond making in the transition state is actually greater in the reaction of PSF as compared with that for PSC.We have thus demonstrated that extensive charge transfer from a nucleophile to a substrate does not necessarily mean a tight bond in the transition state.Moreover the nonzero ρXY values obtained for both PSC and PSF are taken as evidence in support of a common, associative SN2 mechanism for the two halides.