98532-00-4 Usage
Preparation
Over a 1-hr period, the temperature of a stirred solution of 150 gm (0.56 mole) of γ-bromopropylphthalimide, 91.7 gm (0.56 mole) of N-hydroxyphthalimide, 121 gm (1.2 moles) of triethylamine, and 700 ml of dimethyl formamide (DMF) is raised gradually to 90°C. The reaction mixture is cooled to room temperature and poured into 2 liters of water. The precipitate is collected (176 gm, 89.3%; m.p. 177-179°C). Upon re-crystallization (two times from glacial acetic acid, 8ml/gm), the melting point is raised to 178-180°C.
To a solution of 35.0 gm (0.1 mole) of 3-N-phthalimidopropyloxy-N-phthalimide in 200 ml of DMF maintained at 70°C is added 20 gm (0.4 mole) of hydrazine hydrate. After allowing the solution to cool to room temperature over a 1-hr period, 300 ml of cold water is added and the pH of the solution is adjusted to pH 3 with hydrochloric acid. The precipi-tated phthalhydrazide is separated by filtration; the filtrate is evaporated between 40 and 50°C under reduced pressure. The residue is dissolved in 1 liter of methanol and the resulting solution is passed through a column containing 1 liter of IRA-400 ion-exchange resin (in OH" form, and previously treated with methanol). After the eluant is collected the column is rinsed with 1.5 liters of methanol. The eluant and methanol rinsings are combined and concentrated under reduced pressure to afford 3.0 gm (45%), b.p. 110-115°C/3 mm Hg. On redistillation 2 gm (30%) of purified product is isolated; b.p. 99°C/40 mm Hg; n25D 1.4615; d254 0.999.
Check Digit Verification of cas no
The CAS Registry Mumber 98532-00-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,8,5,3 and 2 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 98532-00:
(7*9)+(6*8)+(5*5)+(4*3)+(3*2)+(2*0)+(1*0)=154
154 % 10 = 4
So 98532-00-4 is a valid CAS Registry Number.
InChI:InChI=1/C3H10N2O/c4-2-1-3-6-5/h1-5H2
98532-00-4Relevant academic research and scientific papers
Structural basis of binding and inhibition of ornithine decarboxylase by 1-amino-oxy-3-aminopropane
Aleiwi, Bilal,Bachmann, André S.,Brunzelle, Joseph S.,Ellsworth, Edmund,Lamp, Jared,Melcher, Karsten,Schultz, Chad R.,Suino-Powell, Kelly,Vega, Irving E.,Zhou, X. Edward
, p. 4137 - 4149 (2021/12/27)
Ornithine decarboxylase (ODC) is the rate-limiting enzyme for the synthesis of polyamines (PAs). PAs are oncometabolites that are required for proliferation, and pharmaceutical ODC inhibition is pursued for the treatment of hyperproliferative diseases, including cancer and infectious diseases. The most potent ODC inhibitor is 1-amino-oxy-3-amino-propane (APA). A previous crystal structure of an ODC-APA complex indicated that APA non-covalently binds ODC and its cofactor pyridoxal 5-phosphate (PLP) and functions by competing with the ODC substrate ornithine for binding to the catalytic site. We have revisited the mechanism of APA binding and ODC inhibition through a new crystal structure of APA-bound ODC, which we solved at 2.49 ? resolution. The structure unambiguously shows the presence of a covalent oxime between APA and PLP in the catalytic site, which we confirmed in solution by mass spectrometry. The stable oxime makes extensive interactions with ODC but cannot be catabolized, explaining APA's high potency in ODC inhibition. In addition, we solved an ODC/PLP complex structure with citrate bound at the substrate-binding pocket. These two structures provide new structural scaffolds for developing more efficient pharmaceutical ODC inhibitors.
