2-(1,1,3-trioxo-2,3-dihydro-1,2-benzisothiazol-2-yl)ethyl acetylacetate | 113658-92-7

• 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: 2-(1,1,3-trioxo-2,3-dihydro-1,2-benzisothiazol-2-yl)ethyl acetylacetate
• 英文别名: acetyl acetic acid-2-[N-(1,2-benzisothiazolyl-3(2H)one-1,1-dioxide)]-ethylester；2-(1,1,3-Trioxo-1,2-benzothiazol-2-yl)ethyl 3-oxobutanoate
• CAS: 113658-92-7
• 化学式: C₁₃H₁₃NO₆S
• 分子量: 311.315
• InChiKey: FNKOVJJTKJXFJW-UHFFFAOYSA-N

物化性质

• 沸点：
  509.2±56.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(1,1,3-trioxo-2,3-dihydro-1,2-benzisothiazol-2-yl)ethyl acetylacetate 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 27.0h， 生成 PCA-50941
  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 、 2-(2-羟基乙基)-1,2-苯并异噻唑-3(2H)-酮 1,1-二氧化物 在 三乙胺 作用下， 反应 3.0h， 以88%的产率得到2-(1,1,3-trioxo-2,3-dihydro-1,2-benzisothiazol-2-yl)ethyl 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

• 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。
• 1,4-Dihydropiridines and their use as antithrombotic drugs
  申请人：Alter, S.A.

  公开号：US04782069A1

  公开（公告）日：1988-11-01

  The present invention refers to new 1,4-dihydropyridines, to their obtention processes and to their use as antithrombotic drugs. Said new 1,4-dihdyropyridines have the following general formula (I) ##STR1## wherein R represents hydrogen or a saturated or unsaturated alkyl group, with a linear or branched chain of 1 to 8 carbon atoms, R.sup.1 represents an alkyl radical with a linear, branched or cyclic, saturated or unsaturated chain of 1 to 12 carbon atoms, which may be interrupted by an oxygen or by a 2-(N-salicylamido)ethyl group, n is a number equal to 1 or 2. These new 1,4-dihydropyridines are obtained by processes based on the Hantzch reaction or on modifications thereof.

  本发明涉及新型1,4-二氢吡啶，其制备过程以及作为抗血栓药物的用途。所述新型1,4-二氢吡啶具有以下通式（I）##STR1##其中R代表氢或具有1至8个碳原子的线性或支链饱和或不饱和烷基，R.sup.1代表具有1至12个碳原子的线性、支链或环状饱和或不饱和链的烷基基团，其可以被氧或2-(N-水杨酰胺)乙基基团所中断，n是等于1或2的数字。这些新型1,4-二氢吡啶是通过基于汉茨反应或其修饰的过程获得的。
• SUNKEL, CARLOS;FAU, DE CASA-JUANA MIGUEL;DORREGO, FERNANDO;PRIEGO, JAIME;+
  作者：SUNKEL, CARLOS、FAU, DE CASA-JUANA MIGUEL、DORREGO, FERNANDO、PRIEGO, JAIME、+

  DOI：——

  日期：——
• 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：——
• Synthesis, platelet aggregation inhibitory activity, and in vivo antithrombotic activity of new 1,4-dihydropyridines
  作者：Carlos E. Sunkel、Miguel Fau de Casa-Juana、Francisco Javier Cillero、Jaime G. Priego、M. Pilar Ortega

  DOI：10.1021/jm00118a004

  日期：1988.10

  A series of 1,4-dihydropyridines (DHP) bound to 1,2-benzisothiazol-3-ones were synthesized and evaluated for their ability to inhibit platelet aggregation induced by collagen in human platelet-rich plasma (PRP) and to protect mice against experimental thrombosis. The results showed that the compounds were in vitro inhibitors of collagen-induced platelet aggregation. Most of them were also effective

  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