R-(-)-7-Methoxycarbonyl-5,6,7,8-tetrahydroimidazo<1,5-c>pyrimidin-5-on | 76311-39-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: R-(-)-7-Methoxycarbonyl-5,6,7,8-tetrahydroimidazo<1,5-c>pyrimidin-5-on
• 英文别名: (-)-(R)-5,6,7,8-Tetrahydro-7-methoxycarbonyl-5-oxoimidazo[1,5-c]pyrimidine；methyl (7R)-5-oxo-7,8-dihydro-6H-imidazo[1,5-c]pyrimidine-7-carboxylate
• CAS: 76311-39-2
• 化学式: C₈H₉N₃O₃
• 分子量: 195.178
• InChiKey: MSWBJDHMQDISQH-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  R-(-)-7-Methoxycarbonyl-5,6,7,8-tetrahydroimidazo<1,5-c>pyrimidin-5-on 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 R-(-)-4-(3-Hydroxy-2-methylamino-propyl)-imidazol
  参考文献：
  名称：

  组胺类似物的构效关系，22. Mitt. 对映体 α, Nα-二甲基组胺的绝对构型和组胺样效应

  摘要：

  对映体 α, Nα-二甲基组胺 (+) - 3 和 (-) - 3 的合成，绝对构型的推导和对映体在回肠 (H1) 和心房 (H2) 上的组胺样活性豚鼠进行了描述。

  DOI：

  10.1002/ardp.19803130909
• 作为产物：
  描述：

  R-(-)-Histidinmethylester 以85%的产率得到
  参考文献：
  名称：

  VOCITER, WOLFGANG

  摘要：

  DOI：

文献信息

• Process for preparing N-substituted histidine derivatives
  申请人：Schering Aktiengesellschaft

  公开号：US04937352A1

  公开（公告）日：1990-06-26

  A process is disclosed for the preparation of new N.sup..tau. -substituted histidine derivatives of the general formula ##STR1## According to the process, a histidine derivative of the general formula ##STR2## is reacted with phosgene, and the resultant product is then alkylated and thereafter hydrolyzed with an acid. The products obtained by the process are highly useful for prepration of histidine-analogous proteins and enzymes.

  本发明公开了一种制备新的N.sup..tau. -取代组氨酸衍生物的方法，其化学式为 ##STR1## 根据该方法，首先将一种化学式为 ##STR2## 的组氨酸衍生物与光气反应，然后对产物进行烷基化，最后用酸水解。该方法所得到的产物非常有用，可用于制备组氨酸类蛋白质和酶。
• N.sup..tau. -substituted histidine derivatives
  申请人：Diamalt AG

  公开号：US04772721A1

  公开（公告）日：1988-09-20

  A process is disclosed for the preparation of new N.sup..tau. -substituted histidine derivatives of the general formula ##STR1## According to the process, a histidine derivative of the general formula ##STR2## is reacted with phosgene, and the resultant product is then alkylated and thereafter hydrolyzed with an acid. The products obtained by the process are highly useful for preparation of histidine-analogous proteins and enzymes.

  本发明揭示了一种制备新的N.sup..tau. -取代组氨酸衍生物的方法，其通式为##STR1## 。根据该方法，将通式为##STR2##的组氨酸衍生物与光气反应，然后将所得产物烷基化，最后用酸水解。该方法得到的产物非常有用，可用于制备组氨酸类蛋白质和酶。
• Verfahren zur Herstellung von N-tau-substituierten Histidinderivaten, N-tau-substituierte Histidinderivate und ihre Verwendung
  申请人：DIAMALT AKTIENGESELLSCHAFT

  公开号：EP0129254A2

  公开（公告）日：1984-12-27

  Es wird ein Verfahren zur Herstellung von Nτ-substituierten Histidinderivaten der allgemeinen Formel beschrieben. Gemäß dem Verfahren wird ein Histidinderivat der allgemeinen Formel mit Phosgen umgesetzt, und das erhaltene Produkt wird dann alkyliert und anschließend mit Säure hydrolysiert. Es werden ebenfalls die bei dem Verfehren erhaltenen Produkte und ihre Verwendung beschrieben.

  通式为 Nτ 取代的组氨酸衍生物的制备方法 的工艺。根据该工艺，通式组氨酸衍生物 与光气反应，然后将得到的产物烷基化，随后用酸水解。 还描述了反应中得到的产物及其用途。
• Carnosine protects cardiac myocytes against lipid peroxidation products
  作者：Jingjing Zhao、Dheeraj Kumar Posa、Vijay Kumar、David Hoetker、Amit Kumar、Smirthy Ganesan、Daniel W. Riggs、Aruni Bhatnagar、Michael F. Wempe、Shahid P. Baba

  DOI：10.1007/s00726-018-2676-6

  日期：2019.1

  Endogenous histidyl dipeptides such as carnosine (-alanine-l-histidine) form conjugates with lipid peroxidation products such as 4-hydroxy-trans-2-nonenal (HNE and acrolein), chelate metals, and protect against myocardial ischemic injury. Nevertheless, it is unclear whether these peptides protect against cardiac injury by directly reacting with lipid peroxidation products. Hence, to examine whether changes in the structure of carnosine could affect its aldehyde reactivity and metal chelating ability, we synthesized methylated analogs of carnosine, balenine (-alanine-N-methylhistidine) and dimethyl balenine (DMB), and measured their aldehyde reactivity and metal chelating properties. We found that methylation of N residue of imidazole ring (balenine) or trimethylation of carnosine backbone at N residue of imidazole ring and terminal amine group dimethyl balenine (DMB) abolishes the ability of these peptides to react with HNE. Incubation of balenine with acrolein resulted in the formation of single product (m/z 297), whereas DMB did not react with acrolein. In comparison with carnosine, balenine exhibited moderate acrolein quenching capacity. The Fe2+ chelating ability of balenine was higher than that of carnosine, whereas DMB lacked chelating capacity. Pretreatment of cardiac myocytes with carnosine increased the mean lifetime of myocytes superfused with HNE or acrolein compared with balenine or DMB. Collectively, these results suggest that carnosine protects cardiac myocytes against HNE and acrolein toxicity by directly reacting with these aldehydes. This reaction involves both the amino group of -alanyl residue and the imidazole residue of l-histidine. Methylation of these sites prevents or abolishes the aldehyde reactivity of carnosine, alters its metal-chelating property, and diminishes its ability to prevent electrophilic injury.
• VOELTER, W.;WOLLMANN, H.
  作者：VOELTER, W.、WOLLMANN, H.

  DOI：——

  日期：——