19044-94-1

Basic information

• Product Name: ORYZALIN, DIMETHYL
• Synonyms: ORYZALIN, DIMETHYL
• CAS NO: 19044-94-1
• Molecular Formula: C₁₄H₂₂N₄O₆S
• Molecular Weight: 374.41268
• Mol File: 19044-94-1.mol

Chemical Properties

• Melting Point: 137 °C
• Boiling Point: 496.7°Cat760mmHg
• Flash Point: 254.2°C
• Appearance: /
• Density: 1.324g/cm³
• Vapor Pressure: 5.28E-10mmHg at 25°C
• Refractive Index: 1.567
• PKA: -2.55±0.50(Predicted)
• CAS DataBase Reference: ORYZALIN, DIMETHYL(CAS DataBase Reference)
• NIST Chemistry Reference: ORYZALIN, DIMETHYL(19044-94-1)
• EPA Substance Registry System: ORYZALIN, DIMETHYL(19044-94-1)

Safety Data

• Hazardous Substances Data: 19044-94-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H22N4O6S/c1-5-7-16(8-6-2)14-12(17(19)20)9-11(10-13(14)18(21)22)25(23,24)15(3)4/h9-10H,5-8H2,1-4H3

Upstream product

• 124-40-3 dimethyl amine 
• 37851-36-8 3,5-dinitro-N⁴,N⁴-di-n-propylsulfonyl chloride 
• 38185-06-7 potassium 4-chloro-3,5-dinitrobenzene sulfonate 
• 142-84-7 di-n-propylamine 

Relevant articles and documents

Synthesis and evaluation of oryzalin analogs against Toxoplasma gondii

The synthesis and evaluation of 20 dinitroanilines and related compounds against the obligate intracellular parasite Toxoplasma gondii is reported. Using in vitro cultures of parasites in human fibroblasts, we determined that most of these compounds selectively disrupted Toxoplasma microtubules, and several displayed sub-micromolar potency against the parasite. The most potent compound was N1,N1-dipropyl-2,6-dinitro-4-(trifluoromethyl)-1,3- benzenediamine (18b), which displayed an IC50 value of 36 nM against intracellular T. gondii. Based on these data and another recent report [Ma, C.; Tran, J.; Gu, F.; Ochoa, R.; Li, C.; Sept, D.; Werbovetz, K.; Morrissette, N. Antimicrob. Agents Chemother. 2010, 54, 1453], an antimitotic structure-activity relationship for dinitroanilines versus Toxoplasma is presented.

Synthesis and Antitubulin Activity of N1- and N 4-Substituted 3,5-Dinitro Sulfanilamides against African Trypanosomes and Leishmania

Thirty analogues of N1-phenyl-3,5-dinitro-N4,N 4-di-n-propylsulfanilamide (GB-II-5, compound 3), a new antikinetoplastid antimitotic agent, have been synthesized and evaluated. The addition of simple functional groups to the N1 aromatic ring generally decreases antiparasitic and antimitotic potency, but placement of a dibutyl substituent at the N4 nitrogen to give N1-phenyl-3,5-dinitro-N 4,N4-di-n-butylsulfanilamide (compound 35) augments antitrypanosomal and antileishmanial activity. Compound 35 possesses IC 50 values of 0.12 and 2.6 μM against cultured T. brucei and L. donovani amastigote-like forms, surpassing the activity of compound 3 against these parasites by 3.4- and 1.9-fold, respectively. Compound 35 inhibits the assembly of leishmanial tubulin with an IC50 of 6.9 μM and displays antimitotic effects in cultured T. brucei as assessed by flow cytometry, but shows little effect on purified mammalian tubulin, and displays 100-fold selectivity for trypanosomes over two mammalian cell lines. Although 3 and 35 were not effective in initial in vivo antitrypanosomal assays, the in vitro potency and selectivity of these compounds make N 1-aryl-3,5-dinitro-N4,N4-dialkylsulfanilamides a promising new class of antikinetoplastid agents that act on parasite tubulin.