2-methyl-1,4-benzodioxan-2-carboxylic acid | 68281-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2-methyl-1,4-benzodioxan-2-carboxylic acid
• 英文别名: 2-methyl-2,3-dihydro-benzo[1,4]dioxine-2-carboxylic acid；(2,3-dihydro-2-methyl-1,4-benzodioxin-2-yl)carboxylic acid；2,3-dihydro-2-methyl-1,4-benzodioxin-2-carboxylic acid；2-Methyl-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid；3-methyl-2H-1,4-benzodioxine-3-carboxylic acid
• CAS: 68281-27-6
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: PNXYEGILYPEDQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-1,4-benzodioxan-2-carboxylic acid 在 ammonium hydroxide 、 氯化亚砜 、 phosphorus pentoxide 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 6.0h， 生成 2-cyano-2-methyl-1,4-benzodioxan
  参考文献：
  名称：

  .alpha.-Adrenoreceptor reagents. 3. Synthesis of some 2-substituted 1,4-benzodioxans as selective presynaptic .alpha.2-adrenoreceptor antagonists

  摘要：

  The synthesis and pharmacological activity of a series of 2-substituted derivatives of the selective alpha 2-adrenoreceptor antagonist idazoxan (RX 781094) is described. Substitution in this position by alkyl, alkenyl, cycloalkenyl, and alkoxy groups in many cases gives compounds whose potencies and selectivities are significantly greater than those of the parent compound.

  DOI：

  10.1021/jm00146a013
• 作为产物：
  描述：

  2-hydroxymethyl-2-methyl-2,3-dihydro-1,4-benzodioxin 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 2-methyl-1,4-benzodioxan-2-carboxylic acid
  参考文献：
  名称：

  2,4-Diamino-6,7-dimethoxyquinazolines. 1. 2-[4-(1,4-Benzodioxan-2-ylcarbonyl)piperazin-1-yl] derivatives as .alpha.1-adrenoceptor antagonists and antihypertensive agents

  摘要：

  A series of 4-amino-2-[4-(1,4-benzodioxan-2-ylcarbonyl)piperazin-1 -yl]-6, 7-dimethoxyquinazoline derivatives was synthesized for evaluation as alpha-antagonists and antihypertensive agents. Most compounds displayed high (nM) binding affinity for alpha 1-adrenoceptors with no significant activity at alpha 2-sites. Selective antagonism of the alpha 1-mediated vasoconstrictor effects of norepinephrine is also characteristic of the series. Structure-activity relationships for alpha 1-adrenoceptor affinity are presented, and structural similarity between the 2,4-diamino-6,7-dimethoxyquinazoline nucleus and norepinephrine is established. An alpha 1-receptor model is presented in which charge-reinforced hydrogen bonding is important for binding of both antagonist and agonist molecules. Antihypertensive activity was evaluated after oral administration (5 mg/kg) to spontaneously hypertensive rats, and several compounds displayed similar efficacy to prazosin when assessed after 6 h. On the basis of alpha 1-adrenoceptor affinity/selectivity in vitro and duration of antihypertensive action in vivo, compound 1 (doxazosin) was selected for further evaluation and is currently progressing through phase III clinical trials.

  DOI：

  10.1021/jm00384a009

文献信息

• (2-Alkyl-1,4-benzodioxan-2-yl)carboxylic acids as potential hypolipidemic agents
  作者：Aldo Salimbeni、Elso Manghisi

  DOI：10.1002/jhet.5570170313

  日期：1980.5

  4-benzodioxane, V, and 1,5-benzodioxepine, VII, alcohols. From potassium permanganate oxidation of benzodioxane compounds V the corresponding (2-alkyl-1,4-benzodioxan-2-yl)carboxylic acids II were obtained. In a preliminary pharmacological evaluation benzodioxane acids II did not show any effect on plasma cholesterol, while producing a moderate lowering of triglycerides.

  1，2-二酚与2-烷基-3-氯-1，2-环氧丙烷反应，得到1，4-苯并二恶烷V和1，5-苯并二氧杂庚烷VII的醇的混合物。由高锰酸钾氧化苯并二恶烷化合物V，得到相应的（2-烷基-1，4-苯并二恶烷-2-基）羧酸II。在初步的药理学评估中，苯并二恶烷酸II对血浆胆固醇没有显示任何影响，同时会导致甘油三酸酯的适度降低。
• Benzodioxanyl imidazoline compounds, compositions and use
  申请人：Reckitt & Colman Products Limited

  公开号：US04397860A1

  公开（公告）日：1983-08-09

  Imidazoline derivatives of the formula ##STR1## wherein R.sup.1 is alkyl C.sub.1-7, alkenyl C.sub.2-4, cycloalkenyl C.sub.4-7, cycloalkyl C.sub.4-7 or phenyl; and their non-toxic salts. Processes for the preparation and pharmaceutical compositions thereof. The compounds exhibit presynaptic .alpha..sub.2 -adrenoreceptor antagonism.

  Imidazoline衍生物的化学式为##STR1##，其中R.sup.1为烷基C.sub.1-7，烯基C.sub.2-4，环烯基C.sub.4-7，环烷基C.sub.4-7或苯基；以及它们的无毒盐。其制备方法和药物组合物。这些化合物表现出前突触α2-肾上腺素受体拮抗作用。
• 2,2-Disubstituted 2,3-dihydro-1,4-benzodioxin derivatives having hypotensive activity
  申请人：ISTITUTO LUSO FARMACO D'ITALIA S.p.A.

  公开号：EP0367888A1

  公开（公告）日：1990-05-16

  2,2-Disubstituted 2,3-dihydro-1,4-benzodioxin de­rivatives of formula (I): and pharmaceutically acceptable salts thereof having in vitro high affinity and selectivity for α₁ receptors and in vivo good and long lasting hypotensive activity, with negligeable side-effects; processes for the preparation thereof and pharmaceutical compositions therefrom.

  公式（I）的2,2-二取代2,3-二氢-1,4-苯并二氧杂环己烷衍生物及其药学上可接受的盐具有体外对α₁受体的高亲和力和选择性以及体内良好且持久的降压活性，且副作用可忽略；其制备方法以及由此制备的药物组合物。
• RESIST COMPOSITION, METHOD OF FORMING RESIST PATTERN, COMPOUND, AND ACID DIFFUSION-CONTROLLING AGENT
  申请人：TOKYO OHKA KOGYO CO., LTD.

  公开号：US20220011665A1

  公开（公告）日：2022-01-13

  A resist composition that contains a base material component exhibiting changed solubility in a developing solution under action of acid and a compound (D0) represented by General Formula (d0), in which R 01 , R 02 , R 03 , and R 04 each independently represents a hydrogen atom, a hydroxy group, a halogen atom, or an alkyl group; alternatively, R 01 and R 02 , R 02 and R 03 , or R 03 and R 04 are bonded to each other to form an aromatic ring; R 05 represents a hydrogen atom or an alkyl group; Y represents a group that forms an alicyclic group together with a carbon atom *C; provided that at least one of the carbon atoms that form the alicyclic group is substituted with an ether bond, a thioether bond, a carbonyl group, a sulfinyl group, or a sulfonyl group; m represents an integer of 1 or more, and M m+ represents an m-valent organic cation

  一种抗蚀组合物，包含一种基础材料组分，在酸的作用下在显影溶液中表现出改变的溶解度，以及一种化合物（D0），其通式为（d0），其中R01、R02、R03和R04各自独立地代表氢原子、羟基、卤素原子或烷基；或者，R01和R02、R02和R03、或R03和R04彼此连接形成芳香环；R05代表氢原子或烷基；Y代表与碳原子*C一起形成脂环基的基团；前提是至少有一个形成脂环基的碳原子被醚键、硫醚键、羰基、亚磺酰基或磺酰基取代；m表示1或更多的整数，Mm+表示m价有机阳离子。
• Antihypertensive 4-amino-2-[4-(1,4-benzodioxan-2-carbonyl)
  申请人：Pfizer Inc.

  公开号：US04188390A1

  公开（公告）日：1980-02-12

  Compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein R represents 6,7-di(lower alkoxy) or 6,7,8-tri(lower alkoxy); m is 1 or 2, X is --CHR.sup.1 -- or --CH.sub.2 CH.sub.2 --; each R.sup.1 and R.sup.0 may be the same or different and is hydrogen or lower alkyl; each of R.sup.2 and R.sup.3 is hydrogen, lower alkoxy, lower alkyl, halogen, lower alkanoyl, lower alkoxycarbonyl, --CONR.sup.4 R.sup.5 or --SO.sub.2 NR.sup.4 R.sup.5 wherein each of R.sup.4 and R.sup.5 is hydrogen or lower alkyl; processes for their preparation; and their use as regulators of the cardiovascular system, and particularly in the treatment of hypertension.

  具有以下式子##STR1##和其药学上可接受的盐，其中R代表6,7-二(低烷氧基)或6,7,8-三(低烷氧基)；m为1或2，X为--CHR.sup.1 --或--CH.sub.2 CH.sub.2 --；每个R.sup.1和R.sup.0可以相同或不同，且为氢或低烷基；R.sup.2和R.sup.3中的每一个都为氢、低烷氧基、低烷基、卤素、低烷酰基、低烷氧羰基、--CONR.sup.4 R.sup.5或--SO.sub.2 NR.sup.4 R.sup.5，其中每个R.sup.4和R.sup.5为氢或低烷基；它们的制备过程；以及它们作为心血管系统调节剂的用途，特别是用于治疗高血压。