水黄皮素 | 521-88-0

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 水黄皮素
• 中文别名: 3-甲氧基-2-苯基-4H-呋喃并[2,3-H]-1-苯并吡喃-4-酮；水黄皮次素；干华豆晶4；干华豆晶 4；卡兰金
• 英文名称: karanjin
• 英文别名: 3-methoxy-2-phenyl-4H-furo[2,3-h]chromen-4-one；3-methoxy-2-phenylfuro[2,3-h]chromen-4-one
• CAS: 521-88-0
• 化学式: C₁₈H₁₂O₄
• mdl: MFCD00017406
• 分子量: 292.291
• InChiKey: LKPQNZRGGNOPPU-UHFFFAOYSA-N

物化性质

• 熔点：
  156°C
• 沸点：
  463.0±45.0 °C(Predicted)
• 密度：
  1.36
• 溶解度：
  可溶于丙酮（少许）、氯仿（少许）、甲醇（少许）
• LogP：
  3.290 (est)
• 碰撞截面：
  160.2 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
• 稳定性/保质期：
  按规格使用和贮存，不会发生分解，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.055
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• RTECS号：
  DX1500000
• 海关编码：
  2932999099
• 安全说明：
  S22,S24/25
• WGK Germany：
  3

制备方法与用途

生物活性

Karanjin 是 Fordia cauliflora 中主要的活性呋喃黄酮醇成分。它通过提高 AMPK 的活性，诱导骨骼肌细胞中 GLUT4 易位。此外，Karanjin 还可通过细胞周期阻滞诱导癌细胞死亡，并促进细胞凋亡。

化学性质

Karanjin 为针状结晶，可溶于甲醇、乙醇和 DMSO 等有机溶剂。它来源于水黄皮、水罗伞以及水流豆（Pongamia pinnata）和莫里鱼藤（Derris mollis）。

用途

水黄皮素具有抗结核杆菌的作用。

反应信息

• 作为反应物：
  描述：

  水黄皮素 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以86%的产率得到karanjic acid
  参考文献：
  名称：

  Synthesis of novel benzofuran isoxazolines as protein tyrosine phosphatase 1B inhibitors

  摘要：

  PTPases are considered to be involved in the etiology of diabetes mellitus and neural diseases, such as Alzheimer's disease and Parkinson's disease. Therefore, PTPase inhibitors should be useful tools to Study the role of PTPases in these diseases and other biological phenomena, and which can be developed into chemotherapeutic agents. In the present study, we have synthesized novel benzofuran isoxazolines 13-21 via 1,3-dipolar cycloaddition reaction using karanjin (1) and kanjone (2), isolated from Pongamia pinnata fruits. All the synthesized compounds were evaluated against PTPase enzyme. Compounds 19 and 20 displayed significant inhibitory activity with IC50 values 76 and 81 mu M, respectively. (C) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.01.062
• 作为产物：
  描述：

  3-methoxy-4-oxo-2-phenyl-4H-furo[2,3-h]chromene-8-carboxylic acid ethyl ester 在 喹啉 、 氢氧化钾 、 铜 作用下， 生成 水黄皮素
  参考文献：
  名称：

  苯并呋喃衍生物的合成研究。第一部分 卡兰金的新合成

  摘要：

  以7-羟基-3-甲氧基黄酮-8-醛(II)为原料，采用田中合成苯并呋喃的方法以良好收率合成3-甲氧基黄酮-7,8-呋喃-α-羧酸(IV)并脱羧将喹啉与铜粉制成卡兰金（Ⅰ）。

  DOI：

  10.1246/bcsj.28.273

文献信息

• [EN] ISOTOPE ENHANCED AMBROXOL FOR LONG LASTING AUTOPHAGY INDUCTION<br/>[FR] AMBROXOL À ISOTOPE AMÉLIORÉ POUR INDUCTION D'AUTOPHAGIE DURABLE
  申请人：STC UNM

  公开号：WO2018148113A1

  公开（公告）日：2018-08-16

  The present invention is directed to 13C and/or 2H isotope enhanced ambroxol ("isotope enhanced ambroxol") and its use in the treatment of autophagy infections, especially mycobacterial and other infections, disease states and/or conditions of the lung, such as tuberculosis, especially including drug resistant and multiple drag resistant tuberculosis. Pharmaceutical compositions comprising isotope enhanced amhroxol, alone or in combination with an additional bioactive agent, especially rifamycin antibiotics, including an additional autophagy modulator (an agent which is active to promote or inhibit autophagy), thus being useful against, an autophagy mediated disease state and/or condition), especially an antophagy mediated disease state and/or condition which occurs in the lungs, for example, a Mycobacterium infection. Chronic Obstructive Pulmonary Disease (COPD), asthma, pulmonary fibrosis, cystic fibrosis, Sjogren's disease and lung cancer (small cell and non-small cell lung cancer, among other disease states and/or conditions, especially of the lung. Methods of treating autophagy disease states and/or conditions, especially including autophagy disease states or conditions which occur principally in the lungs of a patient represent a further embodiment of the present invention. An additional embodiment includes methods of synthesizing compounds according to the present invention as otherwise disclosed herein.

  本发明涉及13C和/或2H同位素增强的氨溴索（“同位素增强的氨溴索”）及其在治疗自噬感染，特别是结核分枝杆菌和其他感染、疾病状态和/或肺部疾病条件中的用途，如肺结核，特别是包括耐药和多重耐药结核病。包括同位素增强的氨溴索的药物组合物，单独或与额外的生物活性剂（特别是利福霉素类抗生素，包括额外的自噬调节剂（一种能够促进或抑制自噬的剂），因此对抗自噬介导的疾病状态和/或条件有用），特别是在肺部发生的自噬介导的疾病状态和/或条件，例如分枝杆菌感染。慢性阻塞性肺病（COPD）、哮喘、肺纤维化、囊性纤维化、干燥综合征和肺癌（小细胞和非小细胞肺癌等其他肺部疾病状态和/或条件，特别是肺部疾病状态和/或条件。治疗自噬疾病状态和/或条件的方法，特别包括治疗主要发生在患者肺部的自噬疾病状态或条件的方法，代表本发明的另一实施例。另一实施例包括根据本发明在此披露的其他方法合成化合物的方法。
• [EN] AZABICYCLIC(THIO)AMIDES AS FUNGICIDAL COMPOUNDS<br/>[FR] (THIO)AMIDES AZABICYCLIQUES EN TANT QUE COMPOSÉS FONGICIDES
  申请人：BAYER AG

  公开号：WO2021233861A1

  公开（公告）日：2021-11-25

  The present invention relates to azabicyclic (thio)amide compounds and the uses thereof for controlling phytopathogenic microorganisms such as phytopathogenic fungi. It also relates to processes and intermediates for preparing these compounds

  本发明涉及吡啶环(硫)酰胺化合物及其用途，用于控制植物病原微生物，如植物病原真菌。它还涉及制备这些化合物的过程和中间体。
• PYRIDONE COMPOUNDS AND AGRICULTURAL AND HORTICULTURAL FUNGICIDES CONTAINING THE SAME AS ACTIVE INGREDIENTS
  申请人：MITSUI CHEMICALS AGRO, INC.

  公开号：US20200172486A1

  公开（公告）日：2020-06-04

  Provided are a pyridone compound represented by Formula (1): wherein R1 represents a C1-C6 alkyl group which may be substituted, etc., R2 represents a halogen atom, a cyano group, etc., R3 and R4 are independent to each other, and each represents a hydrogen atom, a C1-C6 alkyl group which may be substituted, etc., or in combination with the nitrogen atom to which they are bonded form a pyrrolidinyl group, a piperidinyl group, etc., which may be substituted, Y represents a phenyl group which may be substituted, etc., X represents an oxygen atom or a sulfur atom, and an agricultural and horticultural fungicide containing the same as an active ingredient.

  提供的是由化学式（1）表示的吡啶酮化合物： 其中 R1代表一个可能被取代的C1-C6烷基，等等， R2代表一个卤素原子，一个氰基，等等， R3和R4彼此独立，每个代表一个氢原子，一个可能被取代的C1-C6烷基，等等，或者与它们结合的氮原子形成一个可能被取代的吡咯啉基团，一个哌啶基团，等等， Y代表一个可能被取代的苯基，等等， X代表一个氧原子或硫原子， 以及含有该化合物作为活性成分的农业和园艺用杀菌剂。
• [EN] ANTIPARASITIC COMPOUNDS<br/>[FR] COMPOSÉS ANTIPARASITAIRES
  申请人：AVISTA PHARMA SOLUTIONS

  公开号：WO2016115315A1

  公开（公告）日：2016-07-21

  The present invention relates to isothiazoline compounds of formula (I). The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to veterinary compositions comprising said compounds.

  本发明涉及式(I)的异噻唑啉化合物。这些化合物对抗或控制无脊椎动物害虫，特别是节肢动物害虫和线虫具有用处。该发明还涉及一种利用这些化合物控制无脊椎动物害虫的方法，以及包含所述化合物的兽药组合物。
• RING-FUSED 2-PYRIDONE DERIVATIVES AND HERBICIDES
  申请人：Takabe Fumiaki

  公开号：US20110287937A1

  公开（公告）日：2011-11-24

  Provided are 2-pyridone derivatives which have excellent herbicidal activity and exhibit high safety to useful crops and so on; salts thereof; and herbicides containing same. In more detail, 2-pyridone derivatives represented by general formula [I] or agrochemically acceptable salts thereof, and herbicides containing these compounds are provided. In general formula [I], X 1 is an oxygen atom or a sulfur atom; X 2 , X 3 , and X 4 are to each CH or N(O) m ; m is an integer of 0 or 1; R 1 is a hydrogen atom, a C 1-12 alkyl group, or the like; R 2 is a halogen atom, a cyano group, or the like; n is an integer of 0 to 4; R 3 is a hydroxyl group, a halogen atom, or the like; A 1 is C(R 11 R 12 ); A 2 is C(R 13 R 14 ) or C═O; A 3 is C(R 15 R 16 ); and R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 are each independently a hydrogen atom or a C 1-6 alkyl group.

  提供了具有优异除草活性并对有用作物等表现出高安全性的2-吡啶酮衍生物；其盐；以及含有这些化合物的除草剂。更详细地说，提供了通式[I]所表示的2-吡啶酮衍生物或其农药可接受的盐，以及含有这些化合物的除草剂。在通式[I]中，X1是氧原子或硫原子；X2、X3和X4分别为CH或N(O)m；m是0或1的整数；R1是氢原子，C1-12烷基或类似物；R2是卤素原子，氰基或类似物；n是0到4的整数；R3是羟基，卤素原子或类似物；A1是C(R11R12)；A2是C(R13R14)或C═O；A3是C(R15R16)；R11、R12、R13、R14、R15和R16分别独立地是氢原子或C1-6烷基基团。