鸢尾黄酮乙素 | 86849-77-6

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 鸢尾黄酮乙素
• 中文别名: 鸢尾甲黄素B
• 英文名称: 5,7,4’-trihydroxy-6,3’-dimethoxyisoflavone
• 英文别名: iristectorigenin A；iristectorigenin B；5,7-dihydroxy-3-(3-hydroxy-4-methoxy-phenyl)-6-methoxy-chromen-4-one；5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-6-methoxychromen-4-one
• CAS: 86849-77-6
• 化学式: C₁₇H₁₄O₇
• 分子量: 330.294
• InChiKey: WRZOUWHPDDOJNR-UHFFFAOYSA-N

物化性质

• 沸点：
  621.2±55.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• 海关编码：
  2914509090

制备方法与用途

化学性质：这是一种白色粉末状物质，能够溶解在甲醇、乙醇和DMSO等有机溶剂中，源自射干。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-6-methoxy-5-propan-2-yloxychromen-4-one	204591-49-1	C20H20O7	372.375
  ——	5,7-dihydroxy-3-(3-hydroxy-4-methoxy-phenyl)-8-methoxy-chromen-4-one	56419-18-2	C17H14O7	330.294
  ——	7-hydroxy-3-(3-hydroxy-4-methoxy-phenyl)-5,8-dimethoxy-chromen-4-one	64640-61-5	C18H16O7	344.321

反应信息

• 作为反应物：
  描述：

  鸢尾黄酮乙素 、 乙酸酐 在 吡啶 作用下， 以100%的产率得到3',5,7-Triacetyl-4',6-dimethoxy-isoflavon
  参考文献：
  名称：

  Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. XXIV. A Convenient Method for Synthesizing 6- and 8-Methoxylated 5,7-Dihydroxyisoflavones.

  摘要：

  自2,4-二羟基-3,6-二甲氧基苯乙酮二苄基醚(3)得到的2',4'-双(苄氧基)-3',6'-二甲氧基查耳酮(5),在甲醇中和硝酸铊(III)氧化重排,产物用氢解还原,闭环得到7-羟基-5,8-二甲氧基异黄酮(8)。这些异黄酮以它们的乙酸盐的接触方法定量地脱甲基,得到5,7-二羟基-8-甲氧基异黄酮(2)。5,7-二羟基-6-甲氧基异黄酮(1)以从2,3-二甲氧基或2-异丙氧基-3-甲氧基-4,6-双(苄氧基)苯乙酮(21)得到的查耳酮为原料,通过相似的方法制得。巯豆另一方面,2'和4'位带有二羟基的异黄酮很易通过下述方法合成。2,2',4,4'-四(苄氧基)-3',6'-二甲氧基查耳酮(5f)的重排产物,在醋酸中用盐酸处理,得到2',4',7-三(苄氧基)-5,8-二甲氧基异黄酮(10f).异黄酮(10f)中的5-甲氧基很快裂解得到相应的5-羟基异黄酮(11f),在无水碳酸钾存在下异构成2',4',7-三(苄氧基)-5-羟基-6-甲氧基异黄酮(25f)。两个5-羟基异黄酮中的苄基很容易氢解,分别得到2',4',5,7-四羟基-8-(2f)和6-甲氧基异黄酮(1f)。这些异黄酮的'C-NMR谱支持了多羟基异黄酮的分子结构的推定。两个天然异黄酮的分子结构进行了修订。

  DOI：

  10.1248/cpb.46.222
• 作为产物：
  描述：

  7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-6-methoxy-5-propan-2-yloxychromen-4-one 在 三氯化铝 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 鸢尾黄酮乙素
  参考文献：
  名称：

  Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. XXIV. A Convenient Method for Synthesizing 6- and 8-Methoxylated 5,7-Dihydroxyisoflavones.

  摘要：

  自2,4-二羟基-3,6-二甲氧基苯乙酮二苄基醚(3)得到的2',4'-双(苄氧基)-3',6'-二甲氧基查耳酮(5),在甲醇中和硝酸铊(III)氧化重排,产物用氢解还原,闭环得到7-羟基-5,8-二甲氧基异黄酮(8)。这些异黄酮以它们的乙酸盐的接触方法定量地脱甲基,得到5,7-二羟基-8-甲氧基异黄酮(2)。5,7-二羟基-6-甲氧基异黄酮(1)以从2,3-二甲氧基或2-异丙氧基-3-甲氧基-4,6-双(苄氧基)苯乙酮(21)得到的查耳酮为原料,通过相似的方法制得。巯豆另一方面,2'和4'位带有二羟基的异黄酮很易通过下述方法合成。2,2',4,4'-四(苄氧基)-3',6'-二甲氧基查耳酮(5f)的重排产物,在醋酸中用盐酸处理,得到2',4',7-三(苄氧基)-5,8-二甲氧基异黄酮(10f).异黄酮(10f)中的5-甲氧基很快裂解得到相应的5-羟基异黄酮(11f),在无水碳酸钾存在下异构成2',4',7-三(苄氧基)-5-羟基-6-甲氧基异黄酮(25f)。两个5-羟基异黄酮中的苄基很容易氢解,分别得到2',4',5,7-四羟基-8-(2f)和6-甲氧基异黄酮(1f)。这些异黄酮的'C-NMR谱支持了多羟基异黄酮的分子结构的推定。两个天然异黄酮的分子结构进行了修订。

  DOI：

  10.1248/cpb.46.222

文献信息

• Preparation of prodrugs for selective drug delivery
  申请人：Mills L. Randell

  公开号：US20050080260A1

  公开（公告）日：2005-04-14

  Synthesis of a chemical compound having the formula A-B-C that may serve for applications such as drug delivery where A is a chemiluminescent, moiety, B is a photochromic moiety, and C is a biologically active moiety where A-B-C may serve as a prodrug. Novel synthetic methods of the present invention to form the prodrug comprised the steps of (1) forming a benzophenone, (2) forming a diaryl ethylene, (3) attaching a phthalimide moiety to at least one of the aryl groups of the ethylene to form a phthalimide-ethylene conjugate, (4) condensing two ethylene-phthalimide conjugates to form a phthalimide-pentadiene conjugate, (5) converting the phthalimide to the phthalhydrazide by reaction with hydrazine to form a carrier compound according to the present invention, and (6) reacting the carrier compound with an nucleophilic moiety of the drug to form the corresponding prodrug. Alternatively the carrier can be prepared by using the halo-substituted diaryl ethylene to make the corresponding cationic leuco dye-like compound with known methods. The cationic compound then is protected by reacting with a nucleophile and coupled with the aminophathalimide by palladium-catalyzed amination to form the protected phthalimide-pentadiene conjugate. The latter is refluxed with hydrazine to convert its phthalimide to the phthalhydrazide and acidified to give the carrier. An additional aspect of the present invention relates to the use of these compounds as antiviral agents for the treatment of viral infections such as HIV and as anticancer agents for the treatment of cancers such as bowel, lung, and breast cancer.

  合成具有A-B-C化学式的化合物，可用于药物传递等应用，其中A是化学发光基团，B是光致变色基团，C是生物活性基团，其中A-B-C可作为前药。本发明的新型合成方法用于形成前药，包括以下步骤：(1)形成苯酮，(2)形成二芳基乙烯，(3)将邻苯二甲酰亚胺基团连接到乙烯的至少一个芳基上，形成邻苯二甲酰亚胺-乙烯共轭物，(4)缩合两个乙烯-邻苯二甲酰亚胺共轭物，形成邻苯二甲酰亚胺-戊二烯共轭物，(5)通过与肼反应将邻苯二甲酰亚胺转化为邻苯二酰肼，形成本发明的载体化合物，(6)将载体化合物与药物的亲核基团反应，形成相应的前药。另外，可以通过使用卤代二芳基乙烯制备相应的阳离子类似的类似类似染料化合物。然后，通过与亲核试剂反应保护阳离子类似化合物，并通过钯催化的胺化与氨基邻苯二甲酰亚胺偶联，形成保护的邻苯二甲酰亚胺-戊二烯共轭物。后者与肼回流，将其邻苯二甲酰亚胺转化为邻苯二酰肼，并酸化以得到载体。本发明的另一个方面涉及将这些化合物用作抗病毒剂，用于治疗病毒感染，如HIV，以及用作抗癌剂，用于治疗结肠癌、肺癌和乳腺癌等癌症。
• Three isoflavone-glycosides from juniperus macropoda
  作者：M.L. Sethi、S.C. Taneja、K.L. Dhar、C.K. Atal

  DOI：10.1016/s0031-9422(00)80107-7

  日期：1983.1

  Abstract Three new isoflavone glycosides have been characterized from the leave of Juniperus macropoda : 5,7-dihydroxy-6,3′,4′-trimethoxyisoflavone 7-glucoside; 5,7,4′-trihydroxy-6,3′,5′-trimethoxyisoflavone 7-glucoside and 5,7,3′-trihydroxy-6,4′-dimethoxyisoflavone 7-diglucoside.

  摘要 从巨足杜松的叶中鉴定出三种新的异黄酮苷：5,7-二羟基-6,3',4'-三甲氧基异黄酮7-葡萄糖苷；5,7,4'-三羟基-6,3',5'-三甲氧基异黄酮7-葡萄糖苷和5,7,3'-三羟基-6,4'-二甲氧基异黄酮7-二葡萄糖苷。
• Isoflavones of Iris spuria
  作者：Abdul S. Shawl、Vishwapaul、Asif Zaman、Ashok K. Kalla

  DOI：10.1016/s0031-9422(00)80573-7

  日期：1984.1

  Abstract A new isoflavone, 5,7-dihydroxy-6,2′-dimethoxyisoflavone, together with iristectorigenin A and iristectorin A were isolated and characterized from the methanol extract of Iris spuria .

  摘要 从伪鸢尾甲醇提取物中分离并表征了一种新的异黄酮，即5,7-二羟基-6,2'-二甲氧基异黄酮，以及鸢尾黄素A和鸢尾素A。
• Renal-selective prodrugs for control of renal sympathetic nerve activity in the treatment of hypertension
  申请人：G.D. Searle & Co.

  公开号：US20030220521A1

  公开（公告）日：2003-11-27

  Renal-selective prodrugs are described which are preferentially converted in the kidney to compounds capable of inhibiting synthesis of catecholamine-type neurotransmitters involved in renal sympathetic nerve activity. The prodrugs described herein are derived from inhibitor compounds capable of inhibiting one or more of the enzymes involved in catecholamine synthesis, such compounds being classifiable as tyrosine hydroxylase inhibitors, or as dopa-decarboxylase inhibitors, or as dopamine-&bgr;-hydroxylase inhibitors. These inhibitor compounds are linked to a chemical moiety, such as a glutamic acid derivative, by a cleavable bond which is recognized selectively by enzymes located predominantly in the kidney. The liberated inhibitor compound is then available in the kidney to inhibit one or more of the enzymes involved in catecholamine synthesis. Inhibition of renal catecholamine synthesis can suppress heightened renal nerve activity associated with sodium-retention related disorders such as hypertension. Conjugates of particular interest are glutamyl derivatives of dopamine-&bgr;-hydroxylase inhibitors, of which N-acetyl-&ggr;-glutamyl fusaric acid hydrazide (shown below) is preferred. 1

  本文描述了一种肾选择性的前药，其在肾脏中优先转化为能够抑制参与肾交感神经活动的儿茶酚型神经递质合成的化合物。本文所描述的前药来源于能够抑制儿茶酚合成中的一个或多个酶的抑制剂化合物，这些化合物可分类为酪氨酸羟化酶抑制剂，多巴脱羧酶抑制剂或多巴胺-&bgr;-羟化酶抑制剂。这些抑制剂化合物通过可被肾脏中大量存在的酶选择性识别的可裂解键与化学基团（如谷氨酸衍生物）连接。释放的抑制剂化合物然后可在肾脏中用于抑制儿茶酚合成中的一个或多个酶。抑制肾脏儿茶酚合成可抑制与钠潴留相关的疾病（如高血压）相关的增强肾脏神经活动。特别感兴趣的共轭物是多巴胺-&bgr;-羟化酶抑制剂的谷氨酰衍生物，其中N-乙酰-&ggr;-谷氨酰富萨酸肼（如下图所示）是首选。1
• Renal-selective prodrugs for control of renal smpathetic nerve activity in the treatment of hypertension
  申请人：G.D. Searle & Co.

  公开号：US20040101523A1

  公开（公告）日：2004-05-27

  Renal-selective prodrugs are described which are preferentially converted in the kidney to compounds capable of inhibiting synthesis of catecholamine-type neurotransmitters involved in renal sympathetic nerve activity. The prodrugs described herein are derived from inhibitor compounds capable of inhibiting one or more of the enzymes involved in catecholamine synthesis, such compounds being classifiable as tyrosine hydroxylase inhibitors, or as dopa-decarboxylase inhibitors, or as dopamine-&bgr;-hydroxylase inhibitors. These inhibitor compounds are linked to a chemical moiety, such as a glutamic acid derivative, by a cleavable bond which is recognized selectively by enzymes located predominantly in the kidney. The liberated inhibitor compound is then available in the kidney to inhibit one or more of the enzymes involved in catecholamine synthesis. Inhibition of renal catecholamine synthesis can suppress heightened renal nerve activity associated with sodium-retention related disorders such as hypertension. Conjugates of particular interest are glutamyl derivatives of dopamine-&bgr;-hydroxylase inhibitors, of which N-acetyl-&ggr;-glutamyl fusaric acid hydrazide (shown below) is preferred. 1

  本文描述了肾脏选择性前药，这些前药被优先转化为能够抑制与肾脏交感神经活动相关的儿茶酚类神经递质合成的化合物。所述前药源自能够抑制儿茶酚类合成中涉及的一个或多个酶的抑制剂化合物，这些化合物可分类为酪氨酸羟化酶抑制剂，或多巴脱羧酶抑制剂，或是多巴胺-β-羟化酶抑制剂。这些抑制剂化合物与化学基团（例如谷氨酸衍生物）通过可被肾脏内的酶特异性识别的可切断键连接。被释放的抑制剂化合物随后可在肾脏中抑制一个或多个涉及儿茶酚类合成的酶。抑制肾脏儿茶酚类合成可以抑制与钠潴留相关的疾病（如高血压）所伴随的过度肾脏神经活动。特别感兴趣的结合物是多巴胺-β-羟化酶抑制剂的谷氨酰衍生物，其中N-乙酰-γ-谷氨酰菌核酸酸肼（如下图所示）是首选。1