NA-SA

NA-SA
Name	NA-SA
Caption	Structural formula of NA-SA
Formula	C10H14N2O2S
Molar mass	214.30 g·mol−1
Appearance	off-white crystalline solid
Density	1.26 g·cm−3
Melting point	128–130 °C
Boiling point	decomposition
Solubility	soluble in ethanol, methanol; low solubility in water

NA-SA NA-SA is a synthetic heterocyclic compound notable for its thiadiazole-derived scaffold and substituted aniline moiety. It has been investigated across multiple fields including agrochemicals, pharmaceuticals, and materials science, and appears in literature alongside investigations into substituted thiadiazole derivatives, aniline analogs, and small-molecule modulators of biochemical pathways. NA-SA's physicochemical profile and synthetic accessibility have made it a subject of study in industrial research programs at laboratories associated with BASF, Syngenta, and university groups at MIT, University of Cambridge, and University of Tokyo.

Etymology and Nomenclature

The trivial name "NA-SA" functions as an alphanumeric code used in patent filings and internal compound libraries rather than an International Union of Pure and Applied Chemistry (IUPAC) systematic name. Similar coding conventions appear in patent literature from DuPont and Bayer where series names such as "X-XX" denote homologous compound sets. The IUPAC name corresponds to a 1,2,3-thiadiazole substituted with an anilino linkage and an alkoxyacetyl side chain; systematic names in related publications reference conventions outlined by the IUPAC nomenclature rules and chemical abstracts indexing employed by CAS.

Chemical Structure and Properties

NA-SA features a five-membered thiadiazole ring bonded to a para-substituted aniline fragment and an acylated alkoxy chain. The molecule's heteroatoms confer moderate polarity and potential hydrogen-bonding capacity, which influence its solubility in organic solvents such as methanol and ethanol while limiting aqueous solubility. Spectroscopic characterization commonly reported includes proton and carbon nuclear magnetic resonance consistent with substituted aromatic and aliphatic resonances, infrared absorptions indicative of amide carbonyl stretches and heterocyclic ring vibrations, and mass spectrometric molecular-ion peaks observed in electrospray ionization studies compliant with analyses from facilities like Agilent Technologies and Thermo Fisher Scientific instrumentation. Crystallographic studies, when available, employ single-crystal X-ray diffraction methods following standards from the International Union of Crystallography.

Synthesis and Production

Reported synthetic routes to NA-SA generally begin with substituted aniline precursors undergoing diazotization or nucleophilic substitution to install the thiadiazole core via cyclization with thiourea derivatives or hydrazine-based intermediates, paralleling methods described in syntheses of 1,2,3-thiadiazole frameworks. Acylation steps utilizing acid chlorides or activated esters introduce the alkoxyacetyl side chain, with coupling reagents analogous to EDC or DCC used in peptide and small-molecule chemistry. Scale-up considerations documented in corporate process chemistry notes from Pfizer and Roche emphasize solvent selection (for example, dichloromethane or toluene), temperature control, and purification strategies including column chromatography and recrystallization aligned with Good Manufacturing Practice (GMP) guidelines from regulatory bodies such as the European Medicines Agency.

Applications and Uses

NA-SA has been explored as a lead scaffold for development of bioactive agents targeting enzymes and receptors implicated in agricultural pest control and mammalian pathologies. Structure–activity relationship campaigns reported in collaboration between academic groups at Harvard University and industrial partners have evaluated NA-SA analogs for activity against insect nicotinic acetylcholine receptor subunits studied in publications alongside imidacloprid and acetamiprid comparisons, and for modulation of kinases where benchmarking occurs against inhibitors like imatinib and sorafenib. Material science investigations reference NA-SA derivatives in the context of organic electronics and dye chemistry related to work on oligothiophenes and porphyrins, examining charge-transport characteristics on substrates such as indium tin oxide.

Health, Safety, and Environmental Impact

Toxicological profiling of NA-SA analogs follows paradigms used in safety assessments by OECD and regulatory toxicology units at NIH and EPA. Acute toxicity studies in rodent models report median lethal dose ranges that necessitate handling precautions; in vitro assays employing human cell lines referenced alongside protocols from ATCC indicate cytotoxicity at micromolar concentrations for certain substitutions. Environmental fate studies mimic procedures used for agrochemical metabolites monitored by USDA and measure persistence in soil and water matrices, potential for bioaccumulation in aquatic organisms assessed similarly to monitoring of pyrethroids, and degradative pathways mediated by microbial consortia studied in microcosm experiments.

Regulation and Handling

Commercial handling and regulatory compliance for NA-SA analogs adhere to chemical inventory and classification systems such as those maintained by REACH in the European Union and TSCA in the United States. Safety data sheets prepared in accordance with GHS standards specify personal protective equipment, engineering controls, and recommended first-aid measures. Transport and storage follow guidelines promulgated by UN model regulations and IATA for air shipment when applicable; waste disposal practices align with protocols issued by national environmental protection agencies including the EPA and Environment Agency (England).

Research and Developments

Recent research directions involving NA-SA and congeners include medicinal chemistry optimization campaigns using high-throughput screening paradigms from facilities such as Broad Institute and structure-based design employing crystallographic complexes deposited in the Protein Data Bank. Computational studies utilize docking and molecular-dynamics workflows consistent with software from Schrödinger and GROMACS, while green chemistry process improvements draw on principles advanced by ACS Green Chemistry Institute. Collaborative projects between industrial laboratories at GlaxoSmithKline and university research groups continue to explore derivative libraries for improved selectivity, reduced toxicity, and enhanced environmental degradability.

Category:Thiadiazoles Category:Anilines Category:Organic compounds