valencic acid | 28090-15-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: valencic acid
• 英文别名: p-[(3-methyl-2-butenyl)oxy]benzoic acid；4-(3-Methylbut-2-enoxy)benzoic acid
• CAS: 28090-15-5
• 化学式: C₁₂H₁₄O₃
• mdl: MFCD11127703
• 分子量: 206.241
• InChiKey: KLZJDQVTNOMAKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  valencic acid 在 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 4-(1H-benzo[d]imidazol-2-yl)phenyl 4-((3-methylbut-2-en-1-yl)oxy)benzoate
  参考文献：
  名称：

  2-Aryl benzazole derived new class of anti-tubercular compounds: Endowed to eradicate mycobacterium tuberculosis in replicating and non-replicating forms

  摘要：

  The high mortality rate and the increasing prevalence of Mtb resistance are the major concerns for the Tuberculosis (TB) treatment in this century. To counteract the prevalence of Mtb resistance, we have synthesized 2-aryl benzazole based dual targeted molecules. Compound 9m and 9n were found to be equally active against replicating and non-replicating form of Mtb (MIC(MABA) 1.98 and 1.66 mu g/ml; MIC(LORA) 2.06 and 1.59 mu g/ml respectively). They arrested the cell division (replicating Mtb) by inhibiting the GTPase activity of FtsZ with IC50 values 45 and 64 mu M respectively. They were also capable of kill Mtb in non-replicating form by inhibiting the biosynthesis of menaquinone which was substantiated by the MenG inhibition (IC50 = 11.62 and 7.49 mu M respectively) followed by the Vit-K2 rescue study and ATP production assay.

  DOI：

  10.1016/j.bioorg.2020.104170
• 作为产物：
  描述：

  1-氯-3-甲基-2-丁烯 在 potassium carbonate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 valencic acid
  参考文献：
  名称：

  2-Aryl benzazole derived new class of anti-tubercular compounds: Endowed to eradicate mycobacterium tuberculosis in replicating and non-replicating forms

  摘要：

  The high mortality rate and the increasing prevalence of Mtb resistance are the major concerns for the Tuberculosis (TB) treatment in this century. To counteract the prevalence of Mtb resistance, we have synthesized 2-aryl benzazole based dual targeted molecules. Compound 9m and 9n were found to be equally active against replicating and non-replicating form of Mtb (MIC(MABA) 1.98 and 1.66 mu g/ml; MIC(LORA) 2.06 and 1.59 mu g/ml respectively). They arrested the cell division (replicating Mtb) by inhibiting the GTPase activity of FtsZ with IC50 values 45 and 64 mu M respectively. They were also capable of kill Mtb in non-replicating form by inhibiting the biosynthesis of menaquinone which was substantiated by the MenG inhibition (IC50 = 11.62 and 7.49 mu M respectively) followed by the Vit-K2 rescue study and ATP production assay.

  DOI：

  10.1016/j.bioorg.2020.104170

文献信息

• Alkylenediamine derivative anti-ulcer drug and antibacterial drug
  申请人：Shiseido Co. Ltd.

  公开号：US05814634A1

  公开（公告）日：1998-09-29

  The invention provides a compound which has anti-ulcer effect and antibacterial activity against Helicobacter pyroli. This compound is an alkylenediamine derivative or salt which has a general formula of (1): ##STR1## wherein each of R.sub.4, R.sub.5, and R.sub.6 is hydrogen or lower alkyl; n represents an integer of 1 to 6; Y is --CH.sub.2 --, --O--, or --N(R.sub.7)--, wherein R.sub.7 is lower alkyl, aryl, carbamoyl lower alkyl, aralkyl, or a heterocyclic group having 5 to 9 carbon numbers; and, W is a group expressed by formulas 2 or 3: ##STR2## wherein (1) in formula 2: each of R.sub.1 and R.sub.2 is hydrogen, lower alkoxy, alkenyloxy, or a halogen atom; each of R.sub.3 and R.sub.3 is methyl, prenyl, or geranyl; when one of R.sub.3 and R.sub.3 is prenyl or geranyl, the other must be a methyl group; and X is oxygen or sulfur; and (2) in formula 3, R.sub.10 is a lower alkyl, and R.sub.11 is a halogen atom.

  该发明提供了一种具有抗溃疡作用和抗幽门螺杆菌活性的化合物。该化合物是一种烷二胺衍生物或盐，其具有通式(1)：##STR1## 其中R.sub.4、R.sub.5和R.sub.6中的每一个是氢或较低的烷基；n表示1到6的整数；Y为--CH.sub.2 --、--O--或--N(R.sub.7)--，其中R.sub.7为较低的烷基、芳基、氨基甲酰较低的烷基、芳基烷基或具有5到9个碳原子的杂环基；W为由式2或3表示的基团：##STR2## 其中在式2中：R.sub.1和R.sub.2中的每一个是氢、较低的烷氧基、烯氧基或卤原子；R.sub.3和R.sub.3中的每一个是甲基、异戊烯基或戊二烯基；当R.sub.3和R.sub.3中的一个是异戊烯基或戊二烯基时，另一个必须是甲基；X为氧或硫；在式3中，R.sub.10为较低的烷基，R.sub.11为卤原子。
• Pyrazolidine derivative radical scavenger brain-infarction depressant
  申请人：Shiseido Co., Ltd.

  公开号：US05849930A1

  公开（公告）日：1998-12-15

  A pyrazolidine derivative or a salt thereof in accordance with the present invention is expressed by the following formula 1: ##STR1## wherein A represents a group expressed by --CH.sub.2 --, --CO--, --CS--, --CH.sub.2 CO--, or --CH.dbd.CH--CO--; B represents a group expressed by --O-- or --NH--; n is an integer of 1 or 2; R represents an alkenyl group; and R.sub.1 and R.sub.2 represent a lower alkyl or benzyl group. The pyrazolidine derivative above mentioned, as a radical scavenger, has antioxidant effect and lipid peroxidation inhibitory activity so as to be available for inhibiting brain infarction or brain edema.

  根据本发明，吡唑啉衍生物或其盐由以下化学式1表示：##STR1##其中A代表由--CH.sub.2 --，--CO--，--CS--，--CH.sub.2 CO--或--CH.dbd.CH--CO--表示的基团；B代表由--O--或--NH--表示的基团；n为1或2的整数；R代表烯基基团；R.sub.1和R.sub.2代表较低的烷基或苄基基团。上述吡唑啉衍生物作为自由基清除剂具有抗氧化作用和抑制脂质过氧化活性，可用于抑制脑梗死或脑水肿。
• Pyrrolidine derivative, anti-ulcer drug, and antibacterial drug
  申请人：Shiseido Co., Ltd.

  公开号：US05925667A1

  公开（公告）日：1999-07-20

  A pyrrolidine derivative or a salt thereof expressed by the following formula 1: ##STR1## wherein R.sub.1 is an alkenyl group; R.sub.2 is a lower alkoxy group or a halogen atom; R.sub.3 is a lower alkyl group; X is a group expressed by --O-- or --S--; Y is carbon or nitrogen atom; m is an integer of 1 to 3; and n is an integer of 0 to 2. The pyrrolidine derivative has an anti-ulcer effect or an antibacterial activity against Helicobacter pyroli, and has also high safety to be available for prevention or cure of ulcers.

  以下是公式1表示的吡咯烷衍生物或其盐：其中R.sub.1是烯基基团；R.sub.2是较低的烷氧基团或卤素原子；R.sub.3是较低的烷基团；X是由--O--或--S--表示的基团；Y是碳或氮原子；m是1到3的整数；n是0到2的整数。该吡咯烷衍生物具有抗溃疡作用或对幽门螺杆菌的抗菌活性，并且对于预防或治疗溃疡具有高度安全性。
• Alkylenediamine derivative, anti-ulcer drug, and antibacterial drug
  申请人：Shiseido Co., Ltd.

  公开号：US06001880A1

  公开（公告）日：1999-12-14

  An alkylenediamine derivative or a salt thereof expressed by the following formula 1: ##STR1## wherein each of R.sub.1 and R.sub.2 represents a lower alkyl group, and W represents a group expressed by any of the following formulas 2 and 3; ##STR2## wherein all variables are as defined in the specification The alkylenediamine derivative has an anti- ulcer effect or an antibacterial activity against Helicobacter pyroli, and has also high safety to be available for prevention or cure of ulcers.

  以下是公式1所表示的烷基二胺衍生物或其盐：其中R.sub.1和R.sub.2各自代表较低的烷基基团，W代表由以下任一公式2和3表示的基团；其中所有变量均如规范中定义的那样。该烷基二胺衍生物具有抗溃疡作用或对幽门螺杆菌具有抗菌活性，并且对于预防或治疗溃疡具有高度安全性。
• Alkynyloxy-phenyl derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US03957833A1

  公开（公告）日：1976-05-18

  Alkynyl, benzyl or phenyl, ethers and esters which are ring substituted with an oxy or a thio aliphatic chain. These ethers and esters are useful in killing and preventing the proliferation of insects by upsetting their hormonal balance.

  炔基、苄基或苯基，醚和酯，其环上被氧或硫代脂肪链取代。这些醚和酯对杀灭和预防昆虫的繁殖具有用处，通过扰乱它们的激素平衡。