4-bromo-1-(diethoxymethyl)-3-methylbenzene | 75986-22-0

• 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: 4-bromo-1-(diethoxymethyl)-3-methylbenzene
• 英文别名: 4-Bromo-3-methylbenzaldehyde diethylacetal；1-bromo-4-(diethoxymethyl)-2-methylbenzene
• CAS: 75986-22-0
• 化学式: C₁₂H₁₇BrO₂
• 分子量: 273.17
• InChiKey: HSHGAXPVAWJKKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  102-104 °C(Press: 0.3 Torr)
• 密度：
  1.254±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-1-(diethoxymethyl)-3-methylbenzene 在 氯化亚砜 、 锌 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 21.0h， 生成 (E)-2-methyl-3-[3-methyl-4-(pyridin-3-ylmethyl)phenyl]acrylic acid ethyl ester
  参考文献：
  名称：

  Highly selective inhibitors of thromboxane synthetase. 2. Pyridine derivatives

  摘要：

  The enzyme thromboxane (TX) synthetase is inhibited by pyridine. The beta-substituted pyridine derivatives showed higher inhibitory potency than the gamma-substituted ones having the same side chain. Among the beta-substituted derivatives containing the omega-carboxyalkyl group, the compounds with 6-8 carbon atoms in the side chain were especially effective. The derivatives holding the phenylene group in the side chain exhibited much higher inhibitory activity than those of the alkylene type. Among them, (E)-3-[4-(3-pyridylmethyl)phenyl]-2-methylacrylic acid hydrochloride (5a) had the highest potency (IC50 = 3 x 10(-9) M). The beta-substituted pyridine derivatives and 1-substituted imidazole derivatives which had the same side chain showed almost the same potency. The beta-substituted pyridine derivatives do not inhibit arachidonic acid cyclooxygenase or prostaglandin I2 synthetase, two other enzymes of the arachidonic cascade.

  DOI：

  10.1021/jm00142a006
• 作为产物：
  描述：

  N-乙酰基-3-甲苯胺 在 盐酸 、 甲醇 、 溴 、 二异丁基氢化铝 、 对甲苯磺酸 、 copper(l) chloride 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 9.5h， 生成 4-bromo-1-(diethoxymethyl)-3-methylbenzene
  参考文献：
  名称：

  Highly selective inhibitors of thromboxane synthetase. 2. Pyridine derivatives

  摘要：

  The enzyme thromboxane (TX) synthetase is inhibited by pyridine. The beta-substituted pyridine derivatives showed higher inhibitory potency than the gamma-substituted ones having the same side chain. Among the beta-substituted derivatives containing the omega-carboxyalkyl group, the compounds with 6-8 carbon atoms in the side chain were especially effective. The derivatives holding the phenylene group in the side chain exhibited much higher inhibitory activity than those of the alkylene type. Among them, (E)-3-[4-(3-pyridylmethyl)phenyl]-2-methylacrylic acid hydrochloride (5a) had the highest potency (IC50 = 3 x 10(-9) M). The beta-substituted pyridine derivatives and 1-substituted imidazole derivatives which had the same side chain showed almost the same potency. The beta-substituted pyridine derivatives do not inhibit arachidonic acid cyclooxygenase or prostaglandin I2 synthetase, two other enzymes of the arachidonic cascade.

  DOI：

  10.1021/jm00142a006

文献信息

• Pyridine alkyl benzoic and thenoic acid compounds and their
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US04427682A1

  公开（公告）日：1984-01-24

  The pyridine derivatives of the general formula: ##STR1## [wherein A represents an alkylene group containing from 1 to 5 carbon atoms unsubstituted or substituted by a hydroxy group, B represents a single bond, or an oxygen or sulphur atom, or an alkylene group containing from 1 to 5 carbon atoms, D represents a single bond, or an alkylene group containing from 1 to 5 carbon atoms, E represents a grouping of the formula: ##STR2## (in which R.sup.6 represents a hydrogen atoms, or an alkyl group containing from 1 to 4 carbon atoms), Z represents a single bond, or an ethynylene group, or a grouping of the formula: ##STR3## in which R.sup.2 represents a hydrogen atom, or an alkyl group containing from 1 to 4 carbon atoms, R.sup.3 represents a hydrogen, bromine or chlorine atom, or an alkyl group containing from 1 to 4 carbon atoms, the symbol represents a single or double bond, the carbon atom attached to R.sup.2 binds to B, and the carbon atom attached to R.sup.3 binds to D, R.sup.1 represents a hydroxy group, or a grouping of the formula: --COOR.sup.4 or --COSR.sup.4, in which R.sup.4 represents a hydrogen atom, or an alkyl group containing from 1 to 12 carbon atoms, or an aralkyl group containing from 7 to 13 carbon atoms, or a cycloalkyl group containing from 4 to 7 carbon atoms unsubstituted or substituted by at least one alkyl group containing from 1 to 4 carbon atoms, or a phenyl group unsubstituted or substituted by at least one halogen atom, trifluoromethyl group, alkyl or alkoxy or alkylthio group containing from 1 to 4 carbon atoms, nitro or phenyl group, R.sup.5 represents a hydrogen atom, or an alkyl group containing from 1 to 4 carbon atoms, with the proviso that, when B represents an oxygen or sulphur atom, Z represents a single bond and D represents an alkylene group containing from 1 to 5 carbon atoms], and non-toxic acid addition salts thereof and, when R.sup.1 represents a carboxy or thiocarboxy group, non-toxic salts thereof, possess a strong inhibitory activity on thromboxane synthetase from rabbit platelet microsomes, and are useful as therapeutically active agents for the treatment or prevention of inflammation, hypertension, thrombus, cerebral apoplexy, asthma, myocardial infarction, cardiostenosis, and cerebral infarction.

  通式为：##STR1## 的吡啶衍生物，其中A表示含有1至5个碳原子的未取代或取代羟基的烷基，B表示单键、氧原子或硫原子，或含有1至5个碳原子的烷基，D表示单键或含有1至5个碳原子的烷基，E表示式：##STR2##（其中R.sup.6表示氢原子或含有1至4个碳原子的烷基），Z表示单键、乙炔基或式：##STR3##（其中R.sup.2表示氢原子或含有1至4个碳原子的烷基，R.sup.3表示氢、溴或氯原子，或含有1至4个碳原子的烷基，符号表示单键或双键，与R.sup.2相连的碳原子与B相连，与R.sup.3相连的碳原子与D相连），R.sup.1表示羟基，或式：--COOR.sup.4或--COSR.sup.4的基团，其中R.sup.4表示氢原子，或含有1至12个碳原子的烷基，或含有7至13个碳原子的芳基烷基，或含有4至7个碳原子的环烷基，未取代或取代至少一个含有1至4个碳原子的烷基，或未取代或取代至少一个卤原子、三氟甲基基团、含有1至4个碳原子的烷基或烷氧基或烷硫基的苯基，或硝基或苯基，R.sup.5表示氢原子或含有1至4个碳原子的烷基，但当B表示氧原子或硫原子，Z表示单键，D表示含有1至5个碳原子的烷基时，不包括其中，以及其无毒酸加合物和当R.sup.1表示羧基或硫代羧基时，其无毒盐，具有对来自兔血小板微粒体的血栓素合酶强烈的抑制活性，并可用于治疗或预防炎症、高血压、血栓、脑卒中、哮喘、心肌梗塞、心脏瓣膜狭窄和脑梗塞等治疗活性剂。
• Pyridine derivatives
  申请人：Ono Pharmaceutical Co., Ltd.,

  公开号：US04271170A1

  公开（公告）日：1981-06-02

  The pyridine derivatives of the general formula: ##STR1## [wherein A represents an alkylene group containing from 1 to 5 carbon atoms unsubstituted or substituted by a hydroxy group, B represents a single bond, or an oxygen or sulphur atom, or an alkylene group containing from 1 to 5 carbon atoms, D represents a single bond, or an alkylene group containing from 1 to 5 carbon atoms, R represents a grouping of the formula: ##STR2## (in which R.sup.6 represents a hydrogen atom, or an alkyl group containing from 1 to 4 carbon atoms), Z represents a single bond, or an ethynylene group, or a grouping of the formula: ##STR3## in which R.sup.2 represents a hydrogen atom, or an alkyl group containing from 1 to 4 carbon atoms, R.sup.3 represents a hydrogen, bromine or chlorine atom, or an alkyl group containing from 1 to 4 carbom atoms; the symbol represents a single or double bond, the carbon atom attached to R.sup.2 binds to B, and the carbon atom attached to R.sup.3 binds to D, R.sup.1 represents a hydroxy group, or a grouping of the formula: --COOR.sup.4 or --COSR.sup.4, in which R.sup.4 represents a hydrogen atom, or an alkyl group containing from 1 to 12 carbon atoms, or an aralkyl group containing from 7 to 13 carbon atoms, or a cycloalkyl group containing from 4 to 7 carbon atoms unsubstituted or substituted by at least one alkyl group containing from 1 to 4 carbon atoms, or a phenyl unsubstituted or substituted by at least one halogen atom, trifluoromethyl group, alkyl or alkoxy or alkylthio group containing from 1 to 4 carbon atoms, nitro or phenyl group, R.sup.5 represents a hydrogen atom, or an alkyl group containing from 1 to 4 carbon atoms, with the proviso that, when B represents an oxygen or sulphur atom, Z represents a single bond and D represents an alkylene group containing from 1 to 5 carbon atoms], and non-toxic acid addition salts thereof and, when R.sup.1 represents a carboxy or thiocarboxy group, non-toxic salts thereof, possess a strong inhibitory activity on thromboxane synthetase from rabbit platelet microsomes, and are useful as therapeutically active agents in the prevention or treatment of inflammation, hypertension, thrombus, cerebral apoplexy, asthma, myocardial infarction, cardiostenosis, cerebral infarction and acute cardiac death.

  通式为：##STR1##的吡啶衍生物[其中A代表含有1至5个碳原子的未取代或取代羟基的烷基，B代表单键，或氧或硫原子，或含有1至5个碳原子的烷基，D代表单键，或含有1至5个碳原子的烷基，R代表公式：##STR2##（其中R.sup.6代表氢原子，或含有1至4个碳原子的烷基），Z代表单键，或乙炔基，或公式：##STR3##（其中R.sup.2代表氢原子，或含有1至4个碳原子的烷基，R.sup.3代表氢、溴或氯原子，或含有1至4个碳原子的烷基；符号代表单键或双键，附在R.sup.2上的碳原子结合在B上，附在R.sup.3上的碳原子结合在D上，R.sup.1代表羟基，或公式：--COOR.sup.4或--COSR.sup.4（其中R.sup.4代表氢原子，或含有1至12个碳原子的烷基，或含有7至13个碳原子的芳基烷基，或含有4至7个碳原子未取代或取代至少一个含有1至4个碳原子的烷基的环烷基，或未取代或取代至少一个卤原子、三氟甲基基团、含有1至4个碳原子的烷基或烷氧基或烷硫基团、硝基或苯基的苯基），R.sup.5代表氢原子，或含有1至4个碳原子的烷基，但是当B代表氧或硫原子，Z代表单键，D代表含有1至5个碳原子的烷基时，则有所限制]及其非毒性酸加合物和当R.sup.1代表羧基或硫代羧基时，其非毒性盐，具有强烈的抑制兔血小板微粒体中的血栓素合成酶的活性，并可作为治疗性活性剂，在预防或治疗炎症、高血压、血栓、脑中风、哮喘、心肌梗死、心脏瓣膜狭窄、脑梗死和急性心脏死亡方面有用。
• S1P receptor modulating compounds and use thereof
  申请人：EPIX Pharmaceuticals, Inc.

  公开号：EP2364976A1

  公开（公告）日：2011-09-14

  The present invention relates to compounds of the general formula (I) that have activity as SIP receptor modulating agents and the use of such compounds to treat diseases associated with inappropriate SIP receptor activity. The compounds may be used as immunomodulators, e.g., for treating or preventing diseases such as autoimmune and related immune disorders including systemic lupus erythematosus, inflammatory bowel diseases such as Crohn's disease and ulcerative colitis, type I diabetes, uveitis, psoriasis, myasthenia gravis, rheumatoid arthritis, non-glomerular nephrosis, hepatitis, Behcet's disease, glomerulonephritis, chronic thrombocytopenic purpura, hemolytic anemia, hepatitis and Wegner's granuloma; and for treating other conditions.

  本发明涉及具有 SIP 受体调节剂活性的通式 (I) 化合物，以及使用此类化合物治疗与不适当的 SIP 受体活性有关的疾病。这些化合物可用作免疫调节剂，例如治疗或预防疾病，如自身免疫性疾病和相关免疫性疾病，包括系统性红斑狼疮、炎症性肠病，如克罗恩病和溃疡性结肠炎、I 型糖尿病、葡萄膜炎、银屑病、重症肌无力、类风湿性关节炎、非肾小球肾炎、肝炎、白塞氏病、肾小球肾炎、慢性血小板减少性紫癜、溶血性贫血、肝炎和韦格纳肉芽肿；以及治疗其他疾病。
• TANOUCHI, TADAO;KAWAMURA, MASANORI;OHYAMA, ISAO;KAJIWARA, IKUO;IGUCHI, YO+, J. MED. CHEM., 1981, 24, N 10, 1149-1155
  作者：TANOUCHI, TADAO、KAWAMURA, MASANORI、OHYAMA, ISAO、KAJIWARA, IKUO、IGUCHI, YO+

  DOI：——

  日期：——
• US4271170A
  申请人：——

  公开号：US4271170A

  公开（公告）日：1981-06-02