甲基2-(3,5-二氯-2,6-二羟基-4-甲基苯甲酰)-5-羟基-3-甲氧基苯甲酸酯 | 2151-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 甲基2-(3,5-二氯-2,6-二羟基-4-甲基苯甲酰)-5-羟基-3-甲氧基苯甲酸酯
• 英文名称: methyl 2-(3,5-dichloro-2,6-dihydroxy-4-methylbenzoyl)-5-hydroxy-3-methoxybenzoate
• 英文别名: dihydrogeodin；dihydrogedin；2-(3,5-dichloro-2,6-dihydroxy-4-methyl-benzoyl)-5-hydroxy-3-methoxy-benzoic acid methyl ester；2-(3,5-Dichlor-2,6-dihydroxy-4-methyl-benzoyl)-5-hydroxy-3-methoxy-benzoesaeure-methylester；Dihydrogeodin
• CAS: 2151-16-8
• 化学式: C₁₇H₁₄Cl₂O₇
• 分子量: 401.2
• InChiKey: AXIPUIQLQUNOCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲基2-(3,5-二氯-2,6-二羟基-4-甲基苯甲酰)-5-羟基-3-甲氧基苯甲酸酯 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以57%的产率得到(+/-)-geodin
  参考文献：
  名称：

  甘丙肽受体亚型GalR1拮抗剂Sch 202596的合成研究：（±）-geodin（Sch 202596的螺香豆香酮部分）的有效合成

  摘要：

  以收敛的方式完成了与Sch 202596（1）的螺香古兰烷酮部分相对应的（±）-geodin [（±）-2 ]的高效合成。该合成方法的特征在于（i）芳基醛6与由芳基溴化物8原位产生的芳基锂7的偶联反应，以递送高度取代的二芳基甲醇24（6 + 7 → 24），以及ii）氧化的螺环化反应。二苯甲酮4构筑必要的螺香豆香烷骨架[ 4 →（±）-2 ]为关键步骤。芳香段图6和图8分别由可商购的3，5-二羟基苯甲酸甲酯（9）和5-甲基间苯二酚（10）制备。

  DOI：

  10.1016/s0040-4020(01)01250-9
• 作为产物：
  描述：

  3,5-二羟基甲苯 在 palladium on activated charcoal sodium chlorite 、 sodium dihydrogenphosphate 、 正丁基锂 、 磺酰氯 、 2-甲基-2-丁烯 、 氢气 、 溴 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 16.67h， 生成 甲基2-(3,5-二氯-2,6-二羟基-4-甲基苯甲酰)-5-羟基-3-甲氧基苯甲酸酯
  参考文献：
  名称：

  甘丙肽受体亚型GalR1拮抗剂Sch 202596的合成研究：（±）-geodin（Sch 202596的螺香豆香酮部分）的有效合成

  摘要：

  以收敛的方式完成了与Sch 202596（1）的螺香古兰烷酮部分相对应的（±）-geodin [（±）-2 ]的高效合成。该合成方法的特征在于（i）芳基醛6与由芳基溴化物8原位产生的芳基锂7的偶联反应，以递送高度取代的二芳基甲醇24（6 + 7 → 24），以及ii）氧化的螺环化反应。二苯甲酮4构筑必要的螺香豆香烷骨架[ 4 →（±）-2 ]为关键步骤。芳香段图6和图8分别由可商购的3，5-二羟基苯甲酸甲酯（9）和5-甲基间苯二酚（10）制备。

  DOI：

  10.1016/s0040-4020(01)01250-9

文献信息

• Studies on metabolites produced by Aspergillus terreus var. aureus. I. Chemical structures and antimicrobial activities of metabolites isolated from culture broth.
  作者：YOSHIHIKO INAMORI、YOSHIAKI KATO、MAYURI KUBO、TERUO KAMIKI、TSUNEMATSU TAKEMOTO、KYOSUKE NOMOTO

  DOI：10.1248/cpb.31.4543

  日期：——

  A fungus which was identified as Aspergillus terreus var. aureus showed antifungal and antibacterial activities. Through the investigation of its metabolites, six compounds (1-6) were isolated ; emodin (1), dihydrogeodin (2), questin (3), sulochrin (5), the new metabolite 2-(3-chloro-4-methyl-γ-resorcyloyl)-5-hydroxy-m-anisic acid methyl ester (4), which is a monochloro derivative of sulochrin (5), and compound (6), the chemical structure of which has not yet been clarified. Dihydrogeodin (2), sulochrin (5), 4 and 6 showed antifungal and antibacterial activities, and 6 had especially strong antifungal activity towards Trichophyton mentagrophytes.

  经鉴定，该真菌为土曲霉变种，具有抗真菌和抗细菌活性。通过对其代谢物的研究，分离出了六种化合物（1-6）：大黄素（1）、二氢大黄素（2）、喹啉（3）、舒洛钦（5）、新代谢物 2-(3-氯-4-甲基-γ-去甲环基)-5-羟基-间甲氧基苯甲酸甲酯（4）（是舒洛钦（5）的单氯衍生物）以及化合物（6），后者的化学结构尚未明确。二氢鬼臼毒素（2）、舒洛钦（5）、4 和 6 具有抗真菌和抗细菌活性，其中 6 对脑毛癣菌具有特别强的抗真菌活性。
• Purification and Characterization of Sulochrin Oxidase from Penicillium frequentans.
  作者：Kexue HUANG、Yasunori YOSHIDA、Kazunobu MIKAWA、Isao FUJII、Yutaka EBIZUKA、Ushio SANKAWA

  DOI：10.1248/bpb.19.42

  日期：——

  Sulochrin oxidase, an enzyme catalyzing regio- and stereospecific phenol oxidative coupling reaction to form (+)-bisdechlorogeodin from sulochrin, was isolated from Penicillium frequentans CMI 96659. By chromatographies on DEAE-cellulose, hydroxyapatite, Phenyl-Sepharose, Mono P, Mono Q, and HPLC gel filtration columns, sulochrin oxidase was purified to apparent homogeneity. The purified enzyme had a molecular weight of 230 K as estimated by gel filtration and 110 K as estimated by sodium dodecylsulfate-polyacrylamide gel electrophoresis under denaturing conditions, suggesting that the active enzyme was a homodimer. The enzyme showed pI 4.0 and an optimum pH of 6. The enzyme activity was strongly inhibited by the copper-chelating reagent, diethyldithiocarbamate, and did not recover its full activity even after removing the inhibitor by dialysis. However, enzyme activity was fully restored by the addition of Cu2+. Thus, sulochrin oxidase is considered to be a copper protein. The enzyme showed high substrate specificity for benzophenone compounds such as sulochrin and dihydrogeodin.

  Sulochrin 氧化酶是一种催化区域特异性和立体特异性苯酚氧化偶联反应的酶，可从 Sulochrin 中形成 (+)-双脱氯乔丁 (Penicillium permanentans CMI 96659)。通过 DEAE-纤维素、羟基磷灰石、Phenyl-Sepharose、Mono P、Mono Q 色谱分析，并用HPLC凝胶过滤柱，将sulochrin氧化酶纯化至表观同质性。纯化酶的分子量通过凝胶过滤估计为230 K，通过十二烷基硫酸钠-聚丙烯酰胺凝胶电泳在变性条件下估计分子量为110 K，这表明活性酶是同型二聚体。该酶的pI为4.0，最适pH为6。该酶活性受到铜螯合剂二乙基二硫代氨基甲酸盐的强烈抑制，即使通过透析除去抑制剂后也没有恢复其全部活性。然而，添加 Cu2+ 后酶活性完全恢复。因此，硫氯蛋白氧化酶被认为是一种铜蛋白。该酶对二苯甲酮化合物（如 Sulochrin 和二氢地黄素）表现出高底物特异性。
• Purification and characterization of dihydrogeodin oxidase from a fungal strain of Aspergillus terreus producing (+)-geodin.
  作者：Isao Fujii、Hiroshi Iijima、Yutaka Ebizuka、Ushio Sankawa

  DOI：10.1248/cpb.31.337

  日期：——

  Dihydrogeodin oxidase (DHGO), an enzyme catalyzing regio- and stereo-specific intramolecular phenol oxidative coupling reaction of dihydrogeodin to give (+)-geodin, was purified up to homogeneity. DHGO was shown to be a blue copper protein with an absorption maximum at 600 nm. The presence of copper atoms was confirmed by atomic absorption analysis. A molecular weight of 153, 000 was estimated for the oxidase and it was composed of two equal molecular weight subunits. DHGO had no phenolase activity and showed strict substrate specificity.

  二氢地奥明氧化酶（DHGO）是一种催化二氢地奥明分子内特定区域和立体定向苯酚氧化偶联反应的酶，可生成（+）-地奥明，其纯度已达到均一性。DHGO是一种蓝铜蛋白，其最大吸收波长为600纳米。原子吸收分析证实了铜原子的存在。氧化酶的分子量为153,000，由两个等分子量的亚基组成。DHGO没有苯酚酶活性，表现出严格的底物特异性。
• Treatment of pulmonary hypertension during surgery with nitric oxide and vasodilators
  作者：Zu Yi Jiang、Tudor Costachescu、Marc Derouin、Gilbert Blaise

  DOI：10.1007/bf03018946

  日期：2000.6

  Purpose: To describe the effects of the combination of several therapies on the pulmonary circulation and cardiac function in a patient with severe pulmonary hypertension.Clinical features: We report the case of a female patient with chronic secondary pulmonary hypertension and cardiac failure who underwent right hemicolectomy under general anesthesia. Insertion of a pulmonary artery catheter before the operation revealed pulmonary artery pressure (PAP) of 55/24 mmHg which was lowered moderately by 40 parts per million (ppm) inhNO, During surgery, the patient presented an episode of atrial fibrillation with a slow, irregular heart rate of 45-50 min(-1) and variable systemic pressure. A dipyridamole DPD (0.2 mg.kg(-1)) bolus stabilized systemic pressure and increased heart rate and cardiac output. However, PAP did not change. Nitroglycerine infusion was started at 10 mg.hr(-1) shortly after the initiation of DPD, The patient responded favourably to combined inhNO, intravenous DPD and NTG therapy with a marked and sustained reduction of PAP and a systemic hemodynamic stability.Conclusion: We conclude that: 1) in combination with inhNO, DPD does not augment the inhNO-induced decrease in PAP; 2) DPD improves the hemodynamic profile and elevates cardiac output; 3) therapeutic combination (inhaled NO, NTG, DPD) has a potent effect an pulmonary pressure in cardiac failure patients.
• Raistrick; Smith, Biochemical Journal, 1936, vol. 30, p. 1315,1319
  作者：Raistrick、Smith

  DOI：——

  日期：——