20153-98-4 Usage
Uses
Used in Pharmaceutical Industry:
Dilazep Dihydrochloride is used as a vasodilator for improving blood flow in the brain and other tissues. It helps in treating conditions related to reduced blood flow and may have potential applications in stroke recovery and prevention.
Used in Neuroscience Research:
Dilazep Dihydrochloride is used as a research compound for studying its neuroprotective properties. It may provide insights into the development of new treatments for neurodegenerative diseases.
Used in Cardiovascular Applications:
As an adenosine uptake inhibitor, Dilazep Dihydrochloride is used to regulate adenosine levels in the body, which can have implications for heart health and blood pressure regulation.
Used in Cancer Research:
Dilazep Dihydrochloride is used as an equilibrative nucleoside transporter inhibitor (ENT 1 and 2) in cancer cell lines. This application helps in understanding the role of these transporters in cancer cell metabolism and the development of targeted cancer therapies.
Used in Angiogenesis Inhibition:
As an angiotensin-converting enzyme inhibitor, Dilazep Dihydrochloride may be used to inhibit angiogenesis, the process through which new blood vessels form. This could be particularly useful in cancer treatment, as it may help to limit the growth of tumors by cutting off their blood supply.
Used in Antiplatelet Therapy:
Dilazep Dihydrochloride acts as an antiplatelet agent, which can be used to prevent blood clot formation. This application is particularly relevant in the treatment and prevention of conditions such as stroke, heart attack, and deep vein thrombosis.
Originator
Cormelian,Asta-Werke,W. Germany,1972
Manufacturing Process
528.8 grams of bis-(3-hydroxypropyl)-ethylene diamine [K. Schlgl and R.
Schlgl, Monatschefte der Chemie 95 (1964) page 935] are dissolved in a
mixture of 1,500 cc of anhydrous ethyl alcohol and 1,250 grams of
triethylamine. 520 grams of 1,3-chlorobromopropane are added thereto
dropwise over a period of about 3 hours while stirring and heating the
reaction mixture in an oil bath of 50°C. After completion of the addition, the
oil bath is heated to 60°C for 20 minutes while stirring of the reaction mixture
is continued. With increasing reaction time, triethylamine hydrochloride is
precipitated. After completion of the reaction, the mixture is allowed to cool to
room temperature.Triethylamine hydrochloride is separated by filtration and the filter cake is
washed with 100 cc of anhydrous ethyl alcohol. The alcohol and the excess of
triethylamine is distilled off in a vacuum of a water pump. The residue
represents a light-yellowish brown viscous oil which is extracted 3 times with
500 cc of anhydrous benzene each time with stirring at 40° to 60°C. The
benzene is distilled off on a water bath at 60°C. Thus, an oil is obtained which
solidifies to a hard mass after some hours. This mass is crushed and dried over P2O5 in an exsiccator. The compound represents N,N'-bis-(3-
hydroxypropyl)homopiperazine. Yield: 128.5 grams. FP: 46°-47°C; BP0.02mm:
141°-142°C.21.6 grams of N,N'-bis-(3-hydroxypropyl)homopiperazine obtained as
described and 63.8 grams of 3,4,5-trimethoxy benzoic acid chloride are
dissolved in 600 parts by volume of anhydrous chloroform. The solution is
heated to boiling for 5 hours. Thereafter, chloroform is distilled off in a
vacuum. The residue is dissolved in water and the aqueous solution is washed
with ether. Thereafter, the aqueous phase is rendered alkaline by the addition
of soda lye and the separated oil base is extracted with ether. The ethereal
solution is dried over Na2SO4. Ether is separated in a vacuum and the highly
viscous residue is dissolved in 150 parts by volume of ethyl alcohol. The
calculated equivalent amount of ethereal HCl is added thereto.The soon crystallizing dihydrochloride is separated by filtration, dried and
recrystallized from 120 parts by volume of ethanol. Thus, after drying for 3
days over P2O5, 40-50 grams (66-70% of the theoretical) of N,N'-bis-[(3,4,5-
trimethoxy benzoloxy)propyl] homopiperazine dihydrochloride containing 1
mol of water of crystallization is obtained. This product has a melting point at
194°-198°C.
Therapeutic Function
Coronary vasodilator
Biochem/physiol Actions
Dilazep is a equilibrative nucleoside transporter 1 (ENTs) inhibitor. It is an antianginal drug and an effective coronary vasodilator. Dilazep elicits anti-albuminuric effects and is an anti-platelet agent. It is a potent adenosine uptake inhibitor and suppresses effects of ischemia.
Check Digit Verification of cas no
The CAS Registry Mumber 20153-98-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,1,5 and 3 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 20153-98:
(7*2)+(6*0)+(5*1)+(4*5)+(3*3)+(2*9)+(1*8)=74
74 % 10 = 4
So 20153-98-4 is a valid CAS Registry Number.
InChI:InChI=1/C31H44N2O10.2ClH/c1-36-24-18-22(19-25(37-2)28(24)40-5)30(34)42-16-8-12-32-10-7-11-33(15-14-32)13-9-17-43-31(35)23-20-26(38-3)29(41-6)27(21-23)39-4;;/h18-21H,7-17H2,1-6H3;2*1H
20153-98-4Relevant academic research and scientific papers
Dilazep analogues for the study of equilibrative nucleoside transporters 1 and 2 (ENT1 and ENT2)
Playa, Hilaire,Lewis, Timothy A.,Ting, Amal,Suh, Byung-Chul,Muoz, Benito,Matuza, Robert,Passer, Brent J.,Schreiber, Stuart L.,Buolamwini, John K.
, p. 5801 - 5804 (2015/01/08)
As ENT inhibitors including dilazep have shown efficacy improving oHSV1 targeted oncolytic cancer therapy, a series of dilazep analogues was synthesized and biologically evaluated to examine both ENT1 and ENT2 inhibition. The central diamine core, alkyl chains, ester linkage and substituents on the phenyl ring were all varied. Compounds were screened against ENT1 and ENT2 using a radio-ligand cell-based assay. Dilazep and analogues with minor structural changes are potent and selective ENT1 inhibitors. No selective ENT2 inhibitors were found, although some analogues were more potent against ENT2 than the parent dilazep.
