15724-26-2

Upstream product

• 2498-50-2 4-aminobenzamidine dihydrochloride 
• 619-72-7 4-nitrobenzonitrile 
• 873-74-5 4-Aminobenzonitrile 
• 15723-90-7 4-nitrobenzamidine hydrochloride 

Relevant academic research and scientific papers

Syntheses of novel 1,3-diazaazulene derivatives and their nonlinear optical characterization

We have synthesized three new 1,3-diazaazulene derivatives, namely, 2-(4′-N,N-dimethylaminophenyl)-6-nitro-1,3-diazaazulene (18, DMAPNA), 2-(4′-aminophenyl)-6-nitro-1,3-diazaazulene (19, APNA) and 2-[4′-N-(2-hydroxyethyl)aminophenyl]-6-nitro-1,3-diazaazulene (20, HEAPNA), each of them contains an amino substitute as the electron donor (D), 2-phenyl-1,3-diazaazulene as the π-conjugated bridge and a nitro as the electron acceptor (A). Our theoretical results have predicted that these D-π-A type chromophores possess low ground-state dipole moment (μg) and large first-order hyperpolarizability (β), which may facilitate a low degree of aggregation for the chromophores dispersed in a polymeric matrix as well as a large nonlinear optical (NLO) response. The expected NLO performance has been confirmed by the experimental β and μg values, e.g., for 18, 407.8 × 10-30 esu and 4.7 D, respectively. The origins of large β and low μg are explained in terms of a two-state quantum model. The DMAPNA (18)-doped and poled polymethylmethacrylate film exhibits a large second harmonic generation (SHG) coefficient of d33 = 10.9 pm V-1 with excellent thermal stability (above 70% of the maximal SHG coefficient remains at ～100 °C). The Royal Society of Chemistry.

Design, Synthesis, and Testing of Potent, Selective Hepsin Inhibitors via Application of an Automated Closed-Loop Optimization Platform

Hepsin is a membrane-anchored serine protease whose role in hepatocyte growth factor (HGF) signaling and epithelial integrity makes it a target of therapeutic interest in carcinogenesis and metastasis. Using an integrated design, synthesis, and screening platform, we were able to rapidly develop potent and selective inhibitors of hepsin. In progressing from the initial hit 7 to compound 53, the IC50 value against hepsin was improved from ～1 μM to 22 nM, and the selectivity over urokinase-type plasminogen activator (uPA) was increased from 30-fold to >6000-fold. Subsequent in vitro ADMET profiling and cellular studies confirmed that the leading compounds are useful tools for interrogating the role of hepsin in breast tumorigenesis.

Design, synthesis and structure-activity relationships of novel diaryl urea derivatives as potential EGFR inhibitors

Two novel series of diaryl urea derivatives 5a-i and 13a-l were synthesized and evaluated for their cytotoxicity against H-460, HT-29, A549, and MDA-MB-231 cancer cell lines in vitro. Therein, 4-aminoquinazolinyl-diaryl urea derivatives 5a-i demonstrated significant activity, and seven of them are more active than sorafenib, with IC50 values ranging from 0.089 to 5.46 μM. Especially, compound 5a exhibited the most active potency both in cellular (IC50 = 0.15, 0.089, 0.36, and 0.75 μM, respectively) and enzymatic assay (IC50 = 56 nM against EGFR), representing a promising lead for further optimization.

Synthesis and biophysical testing of a novel pyrrole-containing polyamide-benzamidine hybrid

This communication details the rationale for the design of a novel polyamide molecule, 1, in which the standard dimethylamino C-terminus functionality has been replaced with a benzamidine moiety. The synthesis of this molecule and the subsequent DNA binding properties, determined from surface plasmon resonance and DNA melts are reported. The benzamidine moiety was shown to significantly increase the binding affinity of the polyamide to its cognate AATTT sequence compared to the parent C-terminus compound 2.

Styrylamidines

Styrylamidines are prepared by treating styrylsulfonylamidines with base. The styrylamidines are effective in the prevention of aggregation of blood platelets and as analgesics. Compounds of the invention are also useful as anticonvulsants, diuretics and antihypertensive agents. The styrylsulfonylamidines of the invention which serve as precursors to the styrylamidines also have analgesic properties. Illustrative of the styrylamidines of the present invention are 4-amino-N-(4-aminostyryl)benzamidine and N-(3,4-dichlorostyryl)acetamidine. An example of a styrylsulfonylamidine is N-(styrylsulfonyl)acetamidine.