Analogues of Oxytocin with Esters of Glutamic Acid Instead of Glutamine in Position 4: Synthesis of a Compound with Idgh

نویسندگان

  • Michal LEBL
  • Tomislav BARTH
  • Karel JOST
چکیده

The reaction of [4-g1utamic acidjdeamlnc-l-carba-oxytocin (lb) with diazoalkanes yielded the corresponding methyl ester Ie and ethyl ester ld. Alternatively, the methyl ester was prepared by means of carbodiimide or thionyl chloride, or by treating the caesium salt of compound Ib with methyl iodide. [2-0~Methyltyrosine, 4-glutamic acid methyl esterjdeamino-f-carba-oxytccin (liz) was also synthetized. The structure of the analogues was verified and their galactogcgic and uteronic activities tested. Compound Ie had the highest galactogogic potency observed as yet (1307 IoU.frog).

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Synthesis and Some Biological Properties and ll-Deamino=4=valine=oxytocin* of 4-Valine-oxytocin

4-Valine-oxytocin and 1-deamino-4-valine-oxytocin, analogues of the posterior pituitary hormone containing a valine residue in place of the glutamine residue in position 4, have been synthesized by the p-nitrophenyl ester method of peptide synthesis and tested for pharmacological activity. The 4-valine-oxytocin possesses 140 units per mg of oxytocic activity and 240 units per mg of avian vasode...

متن کامل

Novel Linezolid like Analogues: Synthesis, Characterization and Biological Evaluation

The synthesis of 4-(substituted benzylidene)-2-(pyrazin-2-yl) oxazol-5(4H)-one was achieved in two steps, In first step, pyrazine-2-carboxamide  dissolved in EtOH, 10% KOH solution with ClCH2COOH produced compound 2-(pyrazine-2-carboxamido) acetic acid (II) and in second step, compound (II) in (CH3CO)2O with aromatic aldehyde, and catalyst potassium ace...

متن کامل

Effect of some oxytocin analogues on natriuresis in rats.

Non-anaesthetized rats were used for studying the relationship between the amount of sodium excreted and structural modifications of oxytocin molecule. Any change performed in position 4 (i.e. the glutamine residue) resulted in a decrease of natriuretic activity as compared to that of oxytocin. The analogues with modifications in the amino-terminal part of the molecule (e.g. substitution of the...

متن کامل

Effect of New Derivatives of Dihydropyridine on Rat Ileal Smooth Muscle in Vitro

In this research we evaluated the calcium channel antagonist activity of various diester analohues of nifedipine on rat ileal smooth muscle.in these analogues,the orthophenyl group at position 4 was replaced by 1 methyl 2-meythylsulfonyl or methylthio 5-imidazolyl.wistar rats(180-250g) were killed by a blow to the head.the intestine was removed above the ileucecal junction and longitudinal smoo...

متن کامل

Oxytocin analogues with amide groups substituted by tetrazole groups in position 4, 5 or 9.

Eleven oxytocin analogues substituted in position 4, 5 or 9 by tetrazole analogues of amino acids were prepared using solid-phase peptide synthesis method and tested for rat uterotonic in vitro and pressor activities, as well as for their affinity to human oxytocin receptor. The tetrazolic group has been used as a bioisosteric substitution of carboxylic, ester or amide groups in structure-activ...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره   شماره 

صفحات  -

تاریخ انتشار 2007