(1,1,3-trioxo-2,3-dihydro-1,2-benzisothiazol-2-yl)methyl acetylacetate | 113658-93-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (1,1,3-trioxo-2,3-dihydro-1,2-benzisothiazol-2-yl)methyl acetylacetate
• 英文别名: acetyl acetic acid-N-(1,2-benzisothiazolyl-3(2H)one-1,1-dioxide)-methylester；(1,1,3-trioxo-1,2-benzothiazol-2-yl)methyl 3-oxobutanoate
• CAS: 113658-93-8
• 化学式: C₁₂H₁₁NO₆S
• 分子量: 297.288
• InChiKey: PMGODMGRZSGXAO-UHFFFAOYSA-N

物化性质

• 沸点：
  494.1±51.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.31
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.82
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1,1,3-trioxo-2,3-dihydro-1,2-benzisothiazol-2-yl)methyl acetylacetate 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 29.0h， 生成 2,6-Dimethyl-5-methoxycarbonyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid-N-(1,2-benzisothiazolyl-3(2H)one-1,1-dioxide)-methylester
  参考文献：
  名称：

  Synthesis of 3-[(2,3-dihydro-1,1,3-trioxo-1,2-benzisothiazol-2-yl)alkyl] 1,4-dihydropyridine-3,5-dicarboxylate derivatives as calcium channel modulators

  摘要：

  1,4-Dihydropyridine (DHP) derivatives with a 1,2-benzisothiazol-3-one 1,1-dioxide group, linked through an alkylene bridge to the C-3 carboxylate of the DHP ring, with both vasconstricting and vasorelaxant properties were obtained. In blocking Ca2+-evoked contractions of K+-depolarized rabbit aortic strips, compounds 12 and 41 were 10-fold more potent than nifedipine; 27 other compounds were 1-4-fold more potent. Their vascular versus cardiac selectivity was very pronounced; for instance, the selectivity index for compound 41 was 70-fold higher than that of nifedipine. This was also true for the vasoconstricting compound 22, which was as potent as Bay K 8644 in enhancing the Ca2+-evoked contractions of rabbit aorta strips, yet it had poor inotropic activity in rabbit left atria. Oral adminstration of compounds 38, 40, 43, and 53 (20 mg/kg) caused a 35-37% decrease in systolic blood pressure in spontaneously hypertensive rats (SHR); these effects were similar to those of nifedipine. However, iv administration of these compounds to anesthetized SHR caused a decrease in blood pressure which was more pronounced and long-lasting than that of nifedipine. When administered iv at 100-mu-g/kg, the vasoconstricting compound 22 caused a 40% increase in systolic and diastolic blood pressure. Compound 22 exhibited an unusually interesting feature over the other five Ca2+ DHP agonists: it had diester substitutions at the C-3 and C-5 positions of the DHP ring. Overall, compounds processing these properties might be useful in treating clinical cardiovascular conditions in which DHP Ca2+ antagonists or agonists are indicated.

  DOI：

  10.1021/jm00091a008
• 作为产物：
  描述：

  双乙烯酮 、 N-羟基甲基糖精 在 mercury(II) diacetate 作用下， 以 溶剂黄146 为溶剂， 以89%的产率得到(1,1,3-trioxo-2,3-dihydro-1,2-benzisothiazol-2-yl)methyl acetylacetate
  参考文献：
  名称：

  新的1,4-二氢吡啶的合成，血小板聚集抑制活性和体内抗血栓形成活性。

  摘要：

  合成了一系列与1,2-苯并噻唑-3结合的1,4-二氢吡啶（DHP），并评估了它们在富含人血小板的血浆（PRP）中抑制胶原蛋白诱导的血小板凝集和保护小鼠免于感染的能力。实验性血栓形成。结果表明该化合物是胶原诱导的血小板聚集的体外抑制剂。它们中的大多数在小鼠抗血栓测定中也有效降低了死亡率。2-（1,1,3-Trioxo-2,3-dihydro-1,2，benzithothiazol-2-yl）ethyl 2,6-二甲基-5-（乙氧基羰基）-4-甲基-1,4-二氢吡啶基羧基（4A）是最有前途的化合物。该化合物在麻醉的猫或麻醉的大鼠中分别以最高750或500微克/ kg的静脉注射剂量均未显示任何心血管作用。同样

  DOI：

  10.1021/jm00118a004

文献信息

• New 1,4-dihydropyridine derivatives, a process for their preparation and their use for influencing the blood flow
  申请人：ALTER, S.A.

  公开号：EP0441736A3

  公开（公告）日：1992-04-22

  The invention relates to new 1,4-dihydropyridine derivatives of the general formula I in which R¹, R², R³ and n have the meaning stated in the patent claims.The compounds of the invention have a vasodilatory effect and are therefore suitable for the treatment of hypertension. Some of the compounds have a vasoconstrictory effect and can therefore be used for the treatment of hypotension.

  本发明涉及通式I的新型1,4-二氢吡啶衍生物，其中R¹、R²、R³和n的含义如专利权利要求中所述。本发明的化合物具有血管舒张作用，因此适用于治疗高血压。其中一些化合物具有血管收缩作用，因此可用于治疗低血压。
• 1,4-dihydropyridine derivatives, a process for their preparation and
  申请人：——

  公开号：US05691361A1

  公开（公告）日：1997-11-25

  The invention relates to new 1,4-dihydropyridine derivatives of the general formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and n have the meaning stated in the patent claims. The compounds of the invention have a vasodilatory effect and are therefore suitable for the treatment of hypertension. Some of the compounds have a vasoconstrictory effect and can therefore be used for the treatment of hypotension.

  本发明涉及一类新的1,4-二氢吡啶衍生物，其通式为I ##STR1## 其中R.sup.1, R.sup.2, R.sup.3 和n的含义在专利权利要求书中有所说明。本发明的化合物具有血管舒张作用，因此适用于治疗高血压。其中一些化合物具有血管收缩作用，因此可用于治疗低血压。
• SUNKEL, CARLOS E.;DE, CASA-JUANA MIGUEL FAU;JAVIER, CILLERO FRANCISCO;PRI+, J. MED. CHEM., 31,(1988) N 10, C. 1886-1890
  作者：SUNKEL, CARLOS E.、DE, CASA-JUANA MIGUEL FAU、JAVIER, CILLERO FRANCISCO、PRI+

  DOI：——

  日期：——