2-propylnaphthalene-1-carbaldehyde | 925441-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-propylnaphthalene-1-carbaldehyde
• 英文别名: 2-propyl-1-naphthaldehyde
• CAS: 925441-42-5
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: RIRKQLUXUYWBEH-UHFFFAOYSA-N

物化性质

• 沸点：
  337.6±11.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-propylnaphthalene-1-carbaldehyde 、 (9aS)-8-acetyl-1,7-dihydroxy-3-methoxy-9a-methyl-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide 在 三乙基硅烷 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 以89%的产率得到(9aS)-8-acetyl-1,7-dihydroxy-3-methoxy-9a-methyl-N-[(2-propylnaphthalen-1-yl)methyl]-9-oxo-9,9a-dihydrodibenzo[b,d]furan-4-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of novel (−)-cercosporamide derivatives as potent selective PPARγ modulators

  摘要：

  Selective peroxisome proliferator-activated receptor gamma (PPAR gamma) modulators are expected to be a novel class of drugs improving plasma glucose levels without PPAR gamma-related adverse effects. As a continuation of our studies for (-)-Cercosporamide derivatives as selective PPAR gamma modulators, we synthesized substituted naphthalene type compounds and identified the most potent compound 15 (EC50 = 0.94 nM, E-max), = 38%). Compound 15 selectively activated PPAR gamma transcription and did not activate PPAR alpha and PPAR delta. The potassium salt of compound 15 showed a high solubility and a good oral bioavailability (58%). Oral administration of the potassium salt remarkably improved the plasma glucose levels of female Zucker diabetic fatty rats at 1 mg/kg. Moreover, it did not cause a plasma volume increase or a cardiac enlargement in Wistar-Imamichi rats, even at 100 mg/kg. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.040
• 作为产物：
  描述：

  1-溴-2-萘甲醛 在 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 、 mineral oil 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 4.5h， 生成 2-propylnaphthalene-1-carbaldehyde
  参考文献：
  名称：

  Synthesis and biological evaluation of novel (−)-cercosporamide derivatives as potent selective PPARγ modulators

  摘要：

  Selective peroxisome proliferator-activated receptor gamma (PPAR gamma) modulators are expected to be a novel class of drugs improving plasma glucose levels without PPAR gamma-related adverse effects. As a continuation of our studies for (-)-Cercosporamide derivatives as selective PPAR gamma modulators, we synthesized substituted naphthalene type compounds and identified the most potent compound 15 (EC50 = 0.94 nM, E-max), = 38%). Compound 15 selectively activated PPAR gamma transcription and did not activate PPAR alpha and PPAR delta. The potassium salt of compound 15 showed a high solubility and a good oral bioavailability (58%). Oral administration of the potassium salt remarkably improved the plasma glucose levels of female Zucker diabetic fatty rats at 1 mg/kg. Moreover, it did not cause a plasma volume increase or a cardiac enlargement in Wistar-Imamichi rats, even at 100 mg/kg. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.040

文献信息

• Strain of streptomyces
  申请人：SANKYO COMPANY LIMITED

  公开号：US20030069204A1

  公开（公告）日：2003-04-10

  The present invention relates to ester, ether and N-alkylcarbamoyl derivatives of compound (Ia) and pharmaceutically acceptable salts thereof. These compounds exhibit excellent antibacterial activity and are useful for the treatment or prevention of bacterial infections. 1 (wherein R 1 is a hydrogen atom or a methyl group; R 2 a is a hydrogen atom, a protecting group for a hydroxy group, or a methyl group; R 3 is a hydrogen atom or a protecting group for a hydroxy group; R 4 a is a hydrogen atom, a hydroxy group or a protected hydroxy group; R 5 is a hydrogen atom or a protecting group for a hydroxy group; and X is a methylene group or a sulfur atom). The invention also includes compounds which are related to the aforeidentified compounds.

  本发明涉及化合物（Ia）的酯、醚和N-烷基氨基甲酰衍生物及其药学上可接受的盐。这些化合物表现出优异的抗菌活性，并可用于治疗或预防细菌感染。其中，R1是氢原子或甲基基团；R2a是氢原子、羟基保护基或甲基基团；R3是氢原子或羟基保护基；R4a是氢原子、羟基或受保护的羟基；R5是氢原子或羟基保护基；X是亚甲基或硫原子。本发明还包括与上述化合物相关的化合物。
• Novel Cercosporamide Derivative
  申请人：Furukawa Akihiro

  公开号：US20090036492A1

  公开（公告）日：2009-02-05

  The present invention relates to a novel cercosporamide derivative, a pharmacologically acceptable salt thereof or an ester thereof which has an excellent hypoglycemic effect and is useful as a therapeutic and/or prophylactic agent for diabetes. A cercosporamide derivative having the general formula (I): [wherein X represents an oxygen atom or the like, R 1 represents a hydrogen atom or a C 1 -C 6 alkyl group, R 2 represents a hydrogen atom, a C 1 -C 6 alkyl group or a C 1 -C 6 halogenated alkyl group, R 3 represents a hydrogen atom or a C 1 -C 6 alkyl group, R 4 represents a C 6 -C 10 aryl group which may be substituted with one to five group(s) independently selected from Substituent Group a, or the like, n represents 1, 2 or 3, and Substituent Group a represents a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 halogenated alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 halogenated alkoxy group, a C 2 -C 6 alkenyloxy group, a C 2 -C 6 alkynyloxy group and the like], a pharmacologically acceptable salt thereof or an ester thereof.

  本发明涉及一种新型的环孢霉素衍生物，其具有优异的降血糖作用，可作为糖尿病治疗和/或预防制剂使用的药物学上可接受的盐或酯。 具有以下通式（I）的环孢霉素衍生物： [其中，X代表氧原子或类似物，R1代表氢原子或C1-C6烷基，R2代表氢原子、C1-C6烷基或C1-C6卤代烷基，R3代表氢原子或C1-C6烷基，R4代表C6-C10芳基，该芳基可被一个到五个独立选择的取代基a取代，n代表1、2或3，取代基a代表卤原子、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6烯氧基、C2-C6炔氧基等]，其药学上可接受的盐或酯。
• NOVEL CERCOSPORAMIDE DERIVATIVE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1914229B1

  公开（公告）日：2010-06-16
• CANNABINOIDS AND DERIVATIVES FOR PROMOTING IMMUNOGENICITY OF TUMOR AND INFECTED CELLS
  申请人：Pascal Biosciences Inc.

  公开号：EP3743061A1

  公开（公告）日：2020-12-02
• [EN] CANNABINOIDS AND DERIVATIVES FOR PROMOTING IMMUNOGENICITY OF TUMOR AND INFECTED CELLS<br/>[FR] CANNABINOÏDES ET LEURS DÉRIVÉS POUR FAVORISER L'IMMUNOGÉNICITÉ DES CELLULES TUMORALES ET INFECTÉES
  申请人：PASCAL BIOSCIENCES INC

  公开号：WO2019144126A1

  公开（公告）日：2019-07-25

  This invention provides processes and compositions for enhancing the immunogenicity of tumor or infected cells by increasing expression of major histocompatibility complex (MHC) class I surface molecules. Tumor cells often circumvent immune recognition by reducing or eliminating MHC expression. The lack of MHC on their surface allows tumor cells to evade immune detection and enables uncontrolled growth. Similarly, certain viral or microbial infections result in MHC class I downregulation and the resulting immune evasion. With a unique reporter assay, we have determined that some cannabinoid compounds and structural analogs can increase MHC class I expression on tumor cells grown in cell culture. The increase of tumor and infected cell MHC class I expression will enable detection and destruction by cytotoxic T-lymphocyte cells. The process and compositions increase the immunogenicity of the target cells, e.g. tumor or infected cells, to enhance their destruction by cytotoxic lymphocytes. When administered in combination, such compositions may enhance the activity of immune- oncology and anti-infectious disease agents.