α-tolyl-α-hydroxypropionic acid | 70588-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: α-tolyl-α-hydroxypropionic acid
• 英文别名: 1-(3-chloropyridazin-6-yl)-3-methyl-1H-pyrazol-5-ol；1-(6-chloropyridazin-3-yl)-3-methyl-1H-pyrazol-5-ol
• CAS: 70588-92-0
• 化学式: C₈H₇ClN₄O
• mdl: MFCD11868241
• 分子量: 210.623
• InChiKey: SZUZPJSZDBWCRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  α-tolyl-α-hydroxypropionic acid 在 碳酸甲丙酯 作用下， 生成 [2-(6-Chloropyridazin-3-yl)-5-methylpyrazol-3-yl] methanesulfonate
  参考文献：
  名称：

  哒嗪衍生物的研究。IV †哒嗪基吡唑的甲磺酸化反应

  摘要：

  上甲磺酰化，1- pyridazinylpyrazoles（1），给予，这取决于取代基和反应条件，Ô -mesylpyrazoles（2）和ö -mesyl -4- Ñ -mesyl -1,4-二氢-4-吡啶基-吡唑衍生物（3）。这些化合物的结构由ir和1 H nmr光谱数据证实。

  DOI：

  10.1002/jhet.5570170432
• 作为产物：
  描述：

  3-氯-6-肼基哒嗪 、 乙酰乙酸乙酯 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 以86%的产率得到α-tolyl-α-hydroxypropionic acid
  参考文献：
  名称：

  哒嗪衍生物的研究。IV †哒嗪基吡唑的甲磺酸化反应

  摘要：

  上甲磺酰化，1- pyridazinylpyrazoles（1），给予，这取决于取代基和反应条件，Ô -mesylpyrazoles（2）和ö -mesyl -4- Ñ -mesyl -1,4-二氢-4-吡啶基-吡唑衍生物（3）。这些化合物的结构由ir和1 H nmr光谱数据证实。

  DOI：

  10.1002/jhet.5570170432

文献信息

• 3-(1-Pyrazolyl)-pyridazine derivatives and hypotensive compositions
  申请人：Richter Gedeon Vegyeszeti Gyar Rt.

  公开号：US04224325A1

  公开（公告）日：1980-09-23

  The invention relates to compounds of general formula ##STR1## wherein R.sup.1 stands for a hydrogen atom or a C.sub.1-6 alkyl-, a C.sub.2-4 hydroxyalkyl, a C.sub.3-6 cycloalkyl or a phenyl group, R.sup.2 stands for a hydrogen, fluorine, chlorine or bromine atom or a C.sub.1-6 alkyl, a C.sub.2-4 hydroxyalkyl, a nitro or an --NR.sup.5 R.sup.6 group, wherein R.sup.5 and R.sup.6 may have the same or different meaning and stand each for a hydrogen atom or a C.sub.1-4 alkyl or a C.sub.2-4 hydroxyalkyl group, R.sup.3 stands for a hydrogen atom or a C.sub.1-6 alkyl, a C.sub.2-4 hydroxyalkyl, a C.sub.3-6 cycloalkyl or a phenyl group, a chlorine atom or a hydroxyl, amino or methoxy group, R.sup.4 stands for a carbamoyl, a cyano or an --NR.sup.7 --NHR.sup.8 group, wherein R.sup.7 and R.sup.8 may have the same or different meaning and stand each for a hydrogen atom or a C.sub.1-4 alkyl, a C.sub.2-4 hydroxyalkyl, a C.sub.1-4 alkoxycarbonyl or an --NR.sup.9 R.sup.10 group, wherein R.sup.9 and R.sup.10 may have the same or different meaning and stand each for a hydrogen atom or a C.sub.1-5 alkyl, a C.sub.2-4 hydroxyalkyl, a C.sub.3-6 cycloalkyl, a phenyl or a benzyl group, or --NR.sup.9 R.sup.10 may represent a morpholine, piperidine or piperazine ring, and their pharmaceutically acceptable acid-addition salts. Furthermore, the invention relates to a process for preparing these compounds. The novel compounds of general formula I have valuable pharmacological properties. Thus they show a considerable hypotensive effect and are capable to inhibit enzymes regulating the catabolism of prostaglandins.

  本发明涉及具有一般式##STR1##的化合物，其中R.sup.1代表氢原子或C.sub.1-6烷基，C.sub.2-4羟基烷基，C.sub.3-6环烷基或苯基，R.sup.2代表氢，氟，氯或溴原子或C.sub.1-6烷基，C.sub.2-4羟基烷基，硝基或--NR.sup.5R.sup.6基团，其中R.sup.5和R.sup.6可以具有相同或不同的含义，分别代表氢原子或C.sub.1-4烷基或C.sub.2-4羟基烷基，R.sup.3代表氢原子或C.sub.1-6烷基，C.sub.2-4羟基烷基，C.sub.3-6环烷基或苯基，氯原子或羟基，氨基或甲氧基基团，R.sup.4代表氨基甲酰基，氰基或--NR.sup.7--NHR.sup.8基团，其中R.sup.7和R.sup.8可以具有相同或不同的含义，分别代表氢原子或C.sub.1-4烷基，C.sub.2-4羟基烷基，C.sub.1-4烷氧羰基或--NR.sup.9R.sup.10基团，其中R.sup.9和R.sup.10可以具有相同或不同的含义，分别代表氢原子或C.sub.1-5烷基，C.sub.2-4羟基烷基，C.sub.3-6环烷基，苯基或苄基，或--NR.sup.9R.sup.10可以表示吗啡啶，哌啶或哌嗪环，并且其药学上可接受的酸加成盐。此外，本发明还涉及制备这些化合物的方法。一般式I的新化合物具有有价值的药理学特性。因此，它们表现出明显的降压作用，并能够抑制调节前列腺素分解代谢的酶。
• Synthesis, Antibacterial and Antioxidant Properties of Pyrazolylpyridazines
  作者：Abdul Qayuum Ather

  DOI：10.14233/ajchem.2013.14590

  日期：——

  A number of 6-chloro-3-(pyrazol-1'-yl) pyridazines were prepared from 3,6-dichloropyridazine via either reaction with hydrazine followed by reaction with appropriate reagents to develop the pyrazole or through a nucleophilic reaction with a pyrazole. Some electrophilic reactions gave the corresponding 4'-substituted pyrazolylpyridazines. All the compounds were tested for their in vitro antibacterial as well as their antioxidant properties.
• Synthesis and identification of novel pyridazinylpyrazolone based diazo compounds as inhibitors of human islet amyloid polypeptide aggregation
  作者：Syed Usama Bin Farrukh、Ibrahim Javed、Abdul Qayyum Ather、Abdul-Hamid Emwas、Meshari Alazmi、Xin Gao、Ghayoor Abbas Chotana、Thomas P. Davis、Pu Chun Ke、Rahman Shah Zaib Saleem

  DOI：10.1016/j.bioorg.2018.11.039

  日期：2019.3

  We have carried out a docking inspired synthesis and screening of a library of diazenyl-derivatives of pyridazinylpyrazolone molecules for their ability to modulate the amyloidogenic self-assembly of human islet amyloid polypeptide (hIAPP). hIAPP is a 37-residue peptide which is involved in glycemic control along with insulin. Its extracellular fibrillar assemblies in pancreatic beta-cells are responsible for type 2 diabetes. A three-step synthetic scheme was used to prepare these novel compounds using 2-(6-chloropyridazin-3-yl) 5 methyl-2,4-dihydro-3H-pyrazol-3-one as a key intermediate that was reacted with various diazo electrophiles to generate a library of compounds with yields ranging from 64 to 85%. The effect of the compounds on hIAPP amyloid fibril formation was evaluated with a thioflavin T (ThT) fluorescence-based kinetic assay. Furthermore, TEM imaging was carried out to corroborate the interactions of the compounds with hIAPP and subsequent hIAPP inhibition at the different level of fibrillization. The CD spectroscopy showed that upon incubation with SSE15314 for 12 h, the percentage of alpha-helices was maintained to a level of hIAPP at 0 h. The current study presents identification and characterization of SSE15314 as the hit, which completely inhibited the fibril formation and can be further optimized into a lead compound.
• SZILAGYI G.; KASZTREINER E.; TARDOS L.; JASZLITS L.; KOSA E.; CSEH G.; TO+, EUR. J. MED. CHEM.-CHIM. THER., 1979, 14, NO 5, 439-445
  作者：SZILAGYI G.、 KASZTREINER E.、 TARDOS L.、 JASZLITS L.、 KOSA E.、 CSEH G.、 TO+

  DOI：——

  日期：——
• MATYUS P.; SZILAGYI G.; KASZTREINER E.; SOHAR P., J. HETEROCYCL. CHEM., 1980, 17, NO 4, 781-783
  作者：MATYUS P.、 SZILAGYI G.、 KASZTREINER E.、 SOHAR P.

  DOI：——

  日期：——