5-formyl-2,3-dihydroxybenzonitrile | 28911-18-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-formyl-2,3-dihydroxybenzonitrile
• CAS: 28911-18-4
• 化学式: C₈H₅NO₃
• 分子量: 163.133
• InChiKey: KANXHIGRABCNET-UHFFFAOYSA-N

物化性质

• 沸点：
  299.9±40.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  哌啶 、 2-硫代乙内酰脲 、 5-formyl-2,3-dihydroxybenzonitrile 以 溶剂黄146 为溶剂， 生成 4-[(3,4-dihydroxy-5-cyanophenyl)methylidene]-2-thioxoimidazolidin-5-one
  参考文献：
  名称：

  Pharmacologically active catechol derivatives

  摘要：

  式(I)的化合物 其中R₁为硝基、卤素、氰基，R₂为从中选择的基团 其中Y为氧或硫；X₁为NR，其中R为氢、C₁-8烷基或苯基 和其药用盐对于预防或治疗由脂质过氧化引起的组织损伤是有用的。

  公开号：

  US05362733A1
• 作为产物：
  描述：

  3-溴-4,5-二甲氧基苯甲醛 在 三溴化硼 作用下， 以 二氯甲烷 、 二甲胺 为溶剂， 反应 4.0h， 生成 5-formyl-2,3-dihydroxybenzonitrile
  参考文献：
  名称：

  某些新型有效的选择性邻苯二酚O-甲基转移酶抑制剂的合成。

  摘要：

  合成了一系列二取代的邻苯二酚衍生物，并测试了其作为潜在的COMT抑制剂的能力。活性最高的化合物在体外的效价（IC50 = 3-6 nM）比已知的COMT抑制剂3'，4'-二羟基-2-甲基苯乙酮（U 0521，IC50 = 6000 nM）高出1000倍以上。新化合物也是高度选择性的COMT抑制剂，对儿茶酚胺的合成和代谢中涉及的其他必需酶没有活性。

  DOI：

  10.1021/jm00124a017

文献信息

• Pharmacologically active compounds, methods for the preparation thereof
  申请人：Orion-yhtyma Oy

  公开号：US04963590A1

  公开（公告）日：1990-10-16

  Pharmacologically active catechol derivatives of formula I ##STR1## wherein R.sub.1 and R.sub.2 independently comprise hydrogen, alkyl, acyl, optionally substituted aroyl, lower alkylsulfonyl or alkylcabamoyl or taken together form a lower alkylidene or cycloalkylidene, X comprises an electronegative substituent such as halogen, nitro, cyano, lower alkylsulfonyl, sulfonamido, aldehyde, caboxyl or trifluoromethyl and R.sub.3 comprises hydrogen, halogen, hydroxy alkyl, amino, nitro, cyano, trifluoromethyl, lower alkylsulfonyl, sulfonamide, aldehyde, alkyl carbonyl, aralkylidene carbonyl or carboxyl or a group selected from ##STR2## wherein R.sub.4 comprises hydrogen, alkyl, cyano, carboxyl or acyl and R.sub.5 comprises hydrogen, cyano, carboxyl, alkoxycarbonyl, carboxyalkenyl, nitro, acyl, optionally substituted aroyl or heteroaroyl, hydroxyalkyl or carboxyalkyl or R.sub.4 and R.sub.5 together form a five to seven membered substituted cycloalkanone ring; --(CO).sub.n (CH.sub.2).sub.m --COR wherein n is 0-1 and m is 0-7 and R comprises hydroxy, alkyl, carboxyalkyl, optionally substituted alkene, alkoxy or optionally substituted amino; ##STR3## wherein R.sub.8 and R.sub.9 independently comprise hydrogen or one of the following optionally substituted groups; alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, or together form an optionally substituted piperidyl group; --NH--CO--R.sub.10 wherein R.sub.10 comprises a substituted alkyl group.

  公式I的药理活性儿茶酚衍生物，其中R.sub.1和R.sub.2独立地包括氢、烷基、酰基、可选择地取代的芳酰基、较低的烷基磺酰基或烷基氨基甲酰基，或者一起形成较低的烷基亚甲基或环烷基亚甲基，X包括电负取代基，如卤素、硝基、氰基、较低的烷基磺酰基、磺胺基、醛基、羧基或三氟甲基，R.sub.3包括氢、卤素、羟基烷基、氨基、硝基、氰基、三
• Small Molecule Xanthine Oxidase Inhibitors and Methods of Use
  申请人：BAYLOR COLLEGE OF MEDICINE

  公开号：US20140163045A1

  公开（公告）日：2014-06-12

  Small molecule xanthine oxidase inhibitors are provided, as well as methods for their use in treating gout or hyperuricemia.

  提供了小分子黄嘌呤氧化酶抑制剂，以及它们在治疗痛风或高尿酸血症中的使用方法。
• Cephalosporins
  申请人：Roussel Uclaf

  公开号：US05455238A1

  公开（公告）日：1995-10-03

  A syn isomer in (R) or (S) form or a mixture thereof of a compound of the formula ##STR1## in the form of an internal salt or a non-toxic, pharmaceutically acceptable acid addition salt wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.5 are individually defined in the specification, R.sub.4 is --OH or alkoxy of 1 to 8 carbon atoms, A and A' are individually selected from the group consisting of hydrogen, an equivalent of an alkali metal or alkaline earth metal, magnesium, ammonium and an organic amine, or one or two of --COOA or --COOA' ARE --CO.sub.2 --, the wavy line means --CH.sub.2 R.sub.6 can be in the E or Z position, R.sub.6 in the quaternary ammonium form is selected from the group consisting of ##STR2## X is defined as in the specification with the proviso that when R.sub.3 is --OH or alkoxy of 1 to 8 carbon atoms, at least one R.sub.1, R.sub.2 and R.sub.5 is other than hydrogen having antibacterial properties.

  一种化合物的同分异构体，其化学式为##STR1##，以内盐或非毒性、药用可接受的酸盐形式存在，其中R.sub.1、R.sub.2、R.sub.3和R.sub.5在说明书中各自定义，R.sub.4为--OH或1至8个碳原子的烷氧基，A和A'分别选自氢、碱金属或碱土金属的等效物、镁、铵和有机胺的群组中，或者--COOA或--COOA'中的一个或两个为--CO.sub.2--，波浪线表示--CH.sub.2 R.sub.6可以处于E或Z位置，R.sub.6以季铵形式选自##STR2##，X的定义如说明书所述，但当R.sub.3为--OH或1至8个碳原子的烷氧基时，至少有一个R.sub.1、R.sub.2和R.sub.5不是氢，具有抗菌性能。
• Catechol derivatives, their physiologically acceptable salts, esters and
  申请人：Orion-yhtyma Oy

  公开号：US05489614A1

  公开（公告）日：1996-02-06

  Known and new catechol derivates may be used as medicinal antioxidants in the prevention or treatment of tissue damage induced by lipid peroxidation. The conditions and diseases to be treated are for example heart disease, rheumatoid arthritis, cancer, inflammatory disease, a rejection reaction in organ transplants, ischemia, cancer and aging.

  已知和新的儿茶酚衍生物可用作药用抗氧化剂，预防或治疗由脂质过氧化引起的组织损伤。需要治疗的疾病和条件包括心脏病、类风湿性关节炎、癌症、炎症性疾病、器官移植的排斥反应、缺血、癌症和衰老。
• Method of treating Parkinson's Disease using pentanedione derivatives
  申请人：Orion-yhtyma Oy

  公开号：US05112861A1

  公开（公告）日：1992-05-12

  The invention concerns a method for the treatment of Parkinson's Disease. The method comprises administering a catechol-O-methyl-transferase inhibiting amount of a compound having the formula I ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, alkylcarbamoyl of 2 to 5 carbon atoms or alkylcarbonyl of 2 to 5 carbon atoms, X represents nitro or cyano and R.sub.3 represents ##STR2## wherein R.sub.4 represents cyano or alkylcarbonyl of 2 to 5 carbon atoms and R.sub.5 represents cyano; alkylcarbonyl of 2 to 5 carbon atoms; or carbamoyl which is unsubstituted or substituted with alkyl of 1 to 8 carbon atoms, or hydroxyalkyl of 1 to 8 carbon atoms or pharmaceutically acceptable salts or esters thereof; and a sufficient amount of levodopa to treat Parkinson's Disease. A peripheral decarboxylase inhibitor such as carbidopa or benzerazide is also preferably administered.

  本发明涉及一种治疗帕金森病的方法。该方法包括向患者施用一种具有以下式子I的化合物，其中R1和R2独立地表示氢、2至5个碳原子的烷基氨基酰基或2至5个碳原子的烷基羰基，X表示硝基或氰基，R3表示下列式子：其中R4表示氰基或2至5个碳原子的烷基羰基，R5表示氰基、2至5个碳原子的烷基羰基、未取代或取代了1至8个碳原子的烷基、1至8个碳原子的羟基烷基的氨基甲酰基或其药学上可接受的盐或酯；以及足够的左旋多巴治疗帕金森病。此外，最好还要施用周围脱羧酶抑制剂，如卡比多巴或苯扎酰胺。