1,3-二-正-丁基黄嘌呤 | 2850-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 1,3-二-正-丁基黄嘌呤
• 中文别名: 1,3-二丁基黄嘌呤
• 英文名称: 1,3-dibutylxanthine
• 英文别名: 1,3-di-n-butylxanthine；1,3-Dibutyl-xanthin；1,3-dibutyl-3,7-dihydro-purine-2,6-dione；SC 2732；1,3-dibutyl-7H-purine-2,6-dione
• CAS: 2850-36-4
• 化学式: C₁₃H₂₀N₄O₂
• 分子量: 264.327
• InChiKey: HDAPVDGMACVEKL-UHFFFAOYSA-N

物化性质

• 熔点：
  185-188°C
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）
• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S22,S36/37/39
• 危险类别码：
  R20/21/22
• 海关编码：
  2933990090
• 储存条件：
  应存于阴凉干燥的环境之中。

反应信息

• 作为反应物：
  描述：

  1,3-二-正-丁基黄嘌呤 在 ruthenium trichloride 、 ammonium sulfate 、 sodium periodate 、 三氯硅烷 、 氨 、 水 、 对甲苯磺酸 、 potassium nonaflate 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 215.0h， 生成 1,3-di-n-butylxanthine 7-(2,3-O-isopropylidene)-β-D-ribofuronic acid
  参考文献：
  名称：

  Selective Ligands for Rat A3 Adenosine Receptors: Structure-Activity Relationships of 1,3-Dialkylxanthine 7-Riboside Derivatives

  摘要：

  1,3-Dibutylxanthine 7-riboside has been found to be a partial agonist at A(3) adenosine receptors (van Galen et al. Mol. Pharmacol. 1994, 45, 1101-1111). 1,3-Dialkylxanthine 7-riboside analogues modified at the 1-, 3-, and 8-purine positions and at the ribose 5'-position were synthesized. The nucleoside analogues were examined for affinity in radioligand binding assays at rat brain A(3) adenosine receptors stably expressed in CHO cells, using the radioligand [[I-125]-4-amino- 3-iodobenzyl]adenosine-5'-N-methyluronamide (AB-MECA). Affinity was assayed at rat brain A(1) and A(2a) receptors using [H-3]PIA and [H-3]CGS 21680, respectively. The affinity of xanthine 7-ribosides at A(3) receptors depended on the 1,3-dialkyl substituents in the order: Pent greater than or equal to. Bu >> Hx > Pr approximate to Me. 1,3-Dipentylxanthine 7-riboside was slightly selective for A(3) receptors (2-fold vs A(1) and 10-fold vs A(2a)). 8-Methoxy substitution was tolerated at A(3) receptors. 2-Thio vs 2-oxo substitution increased potency at all three subtypes and slightly increased A(3) vs A(1) selectivity. The 5'-uronamide modification, which was previously found to enhance A(3) selectivity in N-6-benzyladenosine derivatives, was also incorporated into the xanthine 7-ribosides, with similar results. The affinity of 1,3-dialkylxanthine 7-riboside 5'-uronamides at A(3) receptors depended on the N-alkyluronamide substituent in the order: MeNH > EtNH >> NH2 >> Me(2)N. Affinity of the 5'-uronamides at A(3) receptors was dependent on the 1,3-dialkyl substitution in the order: Bu > Pent > Hex. 1,3-Dibutylxanthine 7-riboside 5'-N-methylcarboxamide, with a K-i value of 229 nM at A(3) receptors, was 160-fold selective for rat A(3) vs A(1) receptors and > 400-fold selective vs A(2a) receptors. This derivative acted as a full agonist in the A(3) receptor-mediated inhibition of adenylate cyclase.

  DOI：

  10.1021/jm00049a021
• 作为产物：
  描述：

  N,N-二正丁基尿素 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 乙酸酐 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium nitrite 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 25.0~80.0 ℃ 、344.73 kPa 条件下， 反应 9.0h， 生成 1,3-二-正-丁基黄嘌呤
  参考文献：
  名称：

  1,3-二烷基黄嘌呤衍生物对大鼠 A3 腺苷受体的构效关系。

  摘要：

  合成了在 8 位取代基上含有羧酸和其他带电基团的 1,3-二烷基黄嘌呤类似物。使用新的放射性配体 [125I]AB-MECA (N6-(4-amino-3-iodobenzyl)adenosine-5'-N-甲基糖醛酰胺），并分别使用 [3H]PIA 和 [3H]CGS 21680 作用于大鼠脑 A1 和 A2a 受体。探索了使用亚氨基二乙酸衍生物在 8 位引入多个羧酸酯基团的合成策略。磺酸盐、羧酸盐或多个羧酸盐基团的存在不会导致对大鼠 A3 受体的亲和力显着增强，尽管如前所述，阴离子基团倾向于降低对 A1 和 A2a 受体的效力。大鼠 A3 受体亲和力不高度依赖于羧酸盐基团与黄嘌呤药效团的距离。2-Thio 与 2-oxo 取代有利于 A3 效力，8-烷基与 8-芳基取代有利于 A3 选择性，尽管很少有衍生物对大鼠 A3 受体具有真正的选择性。1,3-Dimethyl-8-(3-carb

  DOI：

  10.1021/jm00046a022
• 作为试剂：
  描述：

  1,3-二-正-丁基黄嘌呤 、 钠 、 4-溴-1-丁烯 、 sodium hydroxide 在 氮 、 溴化钠 、 1,3-二-正-丁基黄嘌呤 、 氯仿 、 silica gel 、 二氯甲烷,丙烷-2-酮 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 46.0h， 生成 1,3-Di-n-butyl-7-(but-3-enyl)-xanthine
  参考文献：
  名称：

  Pharmaceutical compositions containing xanthines

  摘要：

  一种药物组合物，其关键成分为以下式子的化合物：##STR1## 其中R.sup.1，R.sup.2和R.sup.3中的1至3个表示具有4至8个碳原子的烯基基团，其他的则为具有1至12个碳原子的烷基，而R.sup.1也可以是氢，这些化合物本身和制备它们的过程。

  公开号：

  US04207321A1

文献信息

• Alkylxanthine phosphonates and alkylxanthine phosphine oxides and their
  申请人：Hoechst Aktiengesellschaft

  公开号：US05728686A1

  公开（公告）日：1998-03-17

  Alkylxanthine phosphonates and alkylxanthine phosphine oxides and their use as pharmaceuticals A compound of the formula ##STR1## where R.sup.1 and R.sup.3 are identical or different and at least one of the radicals R.sup.1 and R.sup.3 is a radical of the formula XI ##STR2## in which E is a covalent bond or a (C.sub.1 -C.sub.5)-alkyl, are suitable for the production of pharmaceuticals for the treatment of muscular atrophy, cachexia, muscular dystrophy, sepsis, septic shock, endotoxic shock, systemic inflammation response syndrome, adult respiratory distress syndrome, cerebral malaria, chronic pneumonia, pulmonary sarcoidosis, reperfusion damage, scar formation, inflammation of the bowel and ulcerative colitis, as a result of infections, acquired immune deficiency syndrome, cancer, trauma and other disorders having increased protein loss, peripheral circulatory disorders, disorders having altered leucocyte adhesion, and also disorders which are accompanied by an increased or unregulated tumor necrosis factor production such as rheumatoid arthritis, rheumatoid spondylitis, osteoarthritis and other arthritic disorders.

  烷基黄嘌呤磷酰化合物和烷基黄嘌呤磷酰亚胺氧化物及其作为药物的应用 一种具有以下公式的化合物：##STR1##，其中R.sup.1和R.sup.3相同或不同，且至少一个自由基R.sup.1和R.sup.3是具有以下公式XI的自由基：##STR2##，其中E是共价键或（C.sub.1 -C.sub.5）-烷基，适用于生产用于治疗肌萎缩、恶病质、肌营养不良、败血症、败血性休克、内毒素性休克、系统性炎症反应综合征、成人呼吸窘迫综合征、脑型疟疾、慢性肺炎、肺肉芽肿病、再灌注损伤、疤痕形成、肠炎和溃疡性结肠炎、由于感染、获得性免疫缺陷综合症、癌症、创伤以及其他具有增加蛋白质丢失的疾病、外周循环障碍、具有改变的白细胞粘附的疾病，以及那些伴随有肿瘤坏死因子产生增加或不受控制的疾病，如类风湿性关节炎、强直性脊柱炎、骨关节炎和其他关节疾病。
• A3 adenosine receptor agonists
  申请人：The United States of America as represented by the Department of Health

  公开号：US05773423A1

  公开（公告）日：1998-06-30

  The present invention provides N.sup.6 -benzyladenosine-5'-N-uronamide and related substituted compounds, particularly those containing substituents on the benzyl and/or uronamide groups, and modified xanthine ribosides, as well as pharmaceutical compositions containing such compounds. The present invention also provides a method of selectively activating an A.sub.3 adenosine receptor in a mammal, which method comprises acutely or chronically administering to a mammal in need of selective activation of its A.sub.3 adenosine receptor a therapeutically effective amount of a compound which binds with the A.sub.3 receptor so as to stimulate an A.sub.3 receptor-dependent response.

  本发明提供了N.sup.6-苄基腺苷-5'-N-醛脲和相关的取代化合物，特别是那些在苄基和/或醛脲基团上含有取代基的化合物，以及修饰的黄嘌呤核糖苷，以及含有这些化合物的药物组合物。本发明还提供了一种在哺乳动物中选择性激活A.sub.3腺苷受体的方法，该方法包括向需要选择性激活其A.sub.3腺苷受体的哺乳动物急性或慢性地给予与A.sub.3受体结合的化合物的治疗有效量，以刺激A.sub.3受体依赖的反应。
• Enantioselective and Regiodivergent Addition of Purines to Terminal Allenes: Synthesis of Abacavir
  作者：Niels Thieme、Bernhard Breit

  DOI：10.1002/anie.201610876

  日期：2017.2

  The rhodium‐catalyzed atom‐economic asymmetric N‐selective intermolecular addition of purine derivatives to terminal allenes is reported. Branched allylic purines were obtained in high yields, regioselectivity and outstanding enantioselectivity utilizing a Rh/Josiphos catalyst. Conversely, linear selective allylation of purines could be realized in good to excellent regio‐ and E/Z‐selectivity with

  据报道，铑催化的原子经济不对称的N选择性分子间嘌呤衍生物加成到末端亚丙基上。利用Rh / Josiphos催化剂以高收率，区域选择性和突出的对映选择性获得支链的烯丙基嘌呤。相反，使用Pd / dppf催化剂体系可以实现嘌呤的线性选择性烯丙基化，具有良好的区域选择性和E / Z选择性。此外，新方法被应用于碳环核苷阿巴卡韦的直接不对称合成。
• 8-substituted xanthine derivatives and method of use thereof
  申请人：Beecham Group

  公开号：US05734051A1

  公开（公告）日：1998-03-31

  A method for the treatment of cerebrovascular disorders and/or disorders associated with cerebral senility and/or other disorders which method comprises the administration of an effective, non-toxic amount of a compound of formula (I): ##STR1## or if appropriate a pharmaceutically acceptable salt thereof, wherein R.sup.1 and R.sup.2 each independently represent alkyl or a moiety of formula (a): --(CH.sub.2).sub.m --A (a) wherein m represents zero or an integer 1, 2 or 3; A represents a substituted or unsubstituted cyclic hydrocarbon radical; and R.sup.3 represents a halogen atom, a nitro group, or a group --NR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 each independently represents hydrogen, alkyl or alkylcarbonyl or R.sup.4 and R.sup.5 together with the nitrogen to which they are attached forming an optionally substituted, heterocyclic group; certain novel compounds falling within formula (I) and compositions comprising such compounds.

  一种用于治疗脑血管疾病和/或与脑衰老相关的疾病和/或其他疾病的方法，包括给予化合物（I）的有效、无毒量的给药，其中R.sup.1和R.sup.2各自独立地代表烷基或式（a）的基团：--(CH.sub.2).sub.m --A（a），其中m表示零或整数1、2或3；A表示取代或未取代的环烃基；R.sup.3表示卤原子、硝基基团或基团--NR.sup.4 R.sup.5，其中R.sup.4和R.sup.5各自独立地代表氢、烷基或烷基羰基，或R.sup.4和R.sup.5与它们连接的氮一起形成一个可选择取代的杂环基团；某些落入式（I）的新化合物和包含这些化合物的组合物。
• Method of treating bone loss by stimulation of calcitonin
  申请人：American Home Products Corporation

  公开号：US06221874B1

  公开（公告）日：2001-04-24

  Compounds of the formula R1 and R2 are independently alkyl of 1 to 6 carbon atoms, allyl, or substituted allyl of 3 to 6 carbon atoms; R3 is hydrogen, alkyl of 1 to 6 carbon atoms, or cycloalkyl of 3 to 10 carbon atoms; and R4 is phenyl or naphthyl substituted with alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms or NR5R6; substituted or unsubstituted phenylalkyl wherein the alkyl group contains 1 to 6 carbon atoms; substituted or unsubstituted 5 to 10 membered heteroaryl having 1 to 3 heteroatoms selected from N, S and O; substituted or unsubstituted cycloalkyl of 3 to 10 carbon atoms; or substituted or unsubstituted cycloalkylalkyl of 4 to 10 carbon atoms; provided that phenyl or naphthyl is substituted with NR5R6 when R1 and R2 is alkyl, are useful in the treatment of various disorders associated bone loss by increased transcription and elevation of plasma calcitonin levels. Such disorders include, but are not limited to: Paget's Disease, post menopausal osteoporosis, senile osteoporosis, and glucocorticoid-induced osteoporosis.

  化合物的化学式为R1和R2，分别是烷基（1至6个碳原子）、烯丙基或取代的烯丙基（3至6个碳原子）；R3是氢、烷基（1至6个碳原子）或环烷基（3至10个碳原子）；R4是苯基或萘基，取代有烷基（1至6个碳原子）、烷氧基（1至6个碳原子）或NR5R6；取代或未取代的苯基烷基，其中烷基含1至6个碳原子；取代或未取代的5至10元杂环芳基，含1至3个杂原子，选自N、S和O；取代或未取代的环烷基（3至10个碳原子）；或取代或未取代的环烷基烷基（4至10个碳原子）；若R1和R2为烷基，则苯基或萘基取代为NR5R6。这些化合物可用于治疗与骨质流失相关的各种疾病，通过增加转录和提高血浆降钙素水平。这些疾病包括但不限于：帕吉特病、绝经后骨质疏松症、老年性骨质疏松症和糖皮质激素诱导性骨质疏松症。